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EXAMPLE I
6-Chloro-l-ethyl-7-(4-methylpiperazinyl)-4-oxo-1,4-
dihydroquinoline-3-carboxylic acid
A solution of 4.3 g of 6,7-dichloro-l-ethyl-4-oxo-1,4- dihydro-quinoline-3-carboxylic acid and 9
g of 1一40 methylpiperazine in 45 cm3 of dimethylsulphoxide was stirred and heated to 110°C。
Determination of the Cl ions in the mixture showed that 80% of the theoretical amount of halogen (for the removal of one Cl atom) was in the ionised form after 4 hours of heating. The heating and stirring were continued for a further 3 hours. The reaction product crystallised on cooling. It was filtered off, washed with ethanol and recrystallised from 40 cm3 of methylcellosolve.
2.7 g of 6-chloro-l-ethyl-7-(4-methylpiperazinyl)-4- oxo-1,4-dihydro-quinoline-3-carboxylic acid were obtained; m.p.=260°C.。
  Analysis for (molecular weight 349.8); Calculated %C 58.36, H 5.76, N 12.01, Cl 10.13; Found %C 58.12, H 5.70, N 12.00, Cl 10.48.

Identification
1.75 g of this acid were dissolved in 30 cm3 of 70% aqueous ethanol in the presence of 5 cm3 of N sodium hydroxide and 1.4 cm3 of triethylamine were added. The solution thus obtained was stirred in a hydrogen atmosphere at atmospheric pressure and room tempera ture (230 C.) in thepresence of 0.8 g of 5% palladium on-charcoal which had been previously saturated in the presence of 5 cm3 of ethanol. Absorption (135 cm3; theoretical volume for 1 mol: 121 cm3) ceased after 2 hours 30 minutes. The solution was filtered and concen trated to dryness in vacuo. The residue was dissolved in 20 cm3 of water and mixed with 0.3 cm3 of  acetic  acid. The precipitate (hydrochloride) was recrystallised from 100 cm3 of a saturated aqueous solution of sodium ace tate. The solid was filtered off and recrystallised from methyl cellosolve. 0.65 g of 1-ethyl-7-(4-methylpiperazinyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 215°C., were obtained, which was identical (melting point and infrared spectrum) to the product obtained by the condensation of 1-methylpiperazine with 7-chloro-l-ethyl-4-oxo-1,4-dihydro-quinoline-3-
carboxylic acid.

EXAMPLE 2
A solution of 4.3 g (0.015 mol) of 6,7-dichloro-l- ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid and 9 g of 1-methylpiperazine in a mixture of methyl cellosolve (45 cm3) and dimethylformamide (10 cm3) was heated to reflux temperature. After 6 hours, 75% of the theoretical amount of ionized chlorine (1 atom) had been released into the mixture. Heating was continued for a further 2 hours: The solution was concentrated to dryness in vacuo. The residue was taken up in 20 cm3 of ethanol. The solid, which was filtered off and recrystal lised from methyl cellosolve, gave 2.78 g of 6-chloro-1- ethyl-7-(4-methylpiperazinyl)-4-oxo-1,4-dihydro-quino line-3-carboxylic acid, m.p. 260° C., which was identical to the compound described in Example 1.

EXAMPLE 3

6-Chloro-l-ethyl-4-oxo-7-piperazinyl-1,4-dihydro quinoline-3-carboxylic acid。
2.86 g of 6,7-dichloro-l-ethyl-4-oxo-1,4-dihydro quinoline-3-carboxylic acid and 10 g of piperazine in 30 cm3 of dimethylsulphoxide were stirred and heated to 110° C. After two hours, the reaction was complete. After evaporation of the solvent under a good vacuum, the residue was taken up in 20 cm3 of water. The solid which precipitated was filtered off and recrystallised from 50 cm3 of a mixture of ethanol (1 volume) and methyl cellosolve (1 volume), which enabled an insolu ble impurity, which was separated off by filtration of the hot solution to be removed. The crystals, which precipitated on cooling, were filtered off and recrystal lised from the same solvent mixture. 1.2 g of 6-chloro-1- ethyl-4-oxo-7-piperazinyl-1,4-dihydro-quinoline-3-car boxylic acid were obtained; m.p. 228°-232° C.
Analysis for C16H18CIN303 (molecular 4 weight 335．8): Calculated %C 57.22, H 5.40, N 12.51, CI 10.56; Found %C 56.99, H 5.57, N 12.64; Cl. 10.79.
This product was hygroscopic. In a moist atmo sphere, it absorbed water and gave a dihydrate which lost its water of crystallisation between 100° and 150°C., and then melted at 228°-2300°C: (anhydrous prod uct).
Analysis for C161118CIN303.2 H20 (molecular weight 371.8): Calculated %C 51.68; H 5.96, N 11.30; Found %C51.48;H5.71,N11.11.
EXAMPLE 4
  6-Chloro-l-ethyl-7-[4-(/3-hydroxyethyl)-piperazinyl]-4- oxo-1,4-dihydro-quinoline-3-carboxylic acid
As described in Example 1, 4.3 g of 6,7-dichloro-l- ethyl-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid and 10.6 g of 1一(β-hydroxyethyl)-piperazine in 45 cm3 of DMSO (dimethylsulphoxide) were heated for 3 hours at 110° C. After evaporation of the solvent under a good vacuum, the viscous residue was taken up in 20 cm3 of isopropanol; the mixture was stirred and heated under reflux for 20 minutes. After standing for one night at 40 C:. the solid was filtered off. washed with ethanol And recrystallised from metnyl cellosolve(15cm³

.3.5 g of 6-chloro-l-ethyl-7-[4-(/3-hydroxyethyl)- piperazinyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 2150°C., were obtained.
Analysis for C18H22CIN304(molecular weight 379.5): Calculated %C 59.61, H 5.84, N 11.06, Cl 9.33; Found  %C 57.18, H 5.91, N 11.27, C1 9.18.

EXAMPLE 5
7-(4-Benzylpiperazinyl)-6-chloro-l-ethyl-4-oxo-1,4- 15
dihydro-quinoline-3-carboxylic acid

  A solution of 4.3 g of 6,7-dichloro-l-ethyl-4-oxo-1,4- dihydro-quinoline-3-carboxylic acid and 10.5 g of 1- benzylpiperazine in 45 cm3 of DMSO was stirred and heated to 110° C. After 2 hours, the amount of CI一ions in the reaction mixture corresponded to 94% of the amount calculated for the removal of one halogen atom. After evaporation of the solvent, the reaction product was isolated as in the preceding example; it was purified by recrystallisation from methyl cellosolve. 3.2 g of 7-(4-benzylpiperazinyl)-6-chloro-l-ethyl-4-oxo-1,4- dihydro-quinoline-3-carboxylic acid, m:p. 2280 C.; were obtained.
  Analysis for C23H24CIN303 (molecular weight  425.9): Calculated %C 64.85, H 5.68, N 9.86, Cl 8.32; Found %C 64.73  H 5.82,  N 9.67;  Cl 8.39.
EXAMPLE 6

6-Chloro-l-ethyl-7-(4-formylpiperazinyl)-4-oxo-1;4-
dihydro-3-quinoline carboxylic acid。
  4.3 g of 6;7-dichloro-l-ethyl-4-oxo-1,4-dihydro- quinoline-3-carboxylic acid, 10 g of 1-formylpiperazine and 45 CM3 of DMSO were heated for 3 hours at 10°-1200°C. The reaction product was isolated and purified as in the preceding example: 2 g of 6-chloro-1- ethyl-7-(4-formyl-piperazinyl)-4-oxo-1,4-dihydro- quinoline-3-carboxylic acid, which melted with decom- position at about 3000 C., were obtained.
  Analysis for C17H1gCIN304 (molecular weight 363.79): Calculated %C 56.12, H 4.98; N 11.55, CI 9:74; Found %C 56.13, H 5.19, N 11.42, Cl 9.70。

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