Pyrrolidine → 6,8-Difluoro-1,4-dihydro-4-oxo-1-(4-fluorophenyl)-7-(1-pyrrolidinyl)-quinoline-3-carboxylic acid

HRID 703083Notes

Reaction equation

HRID 703083 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24].[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[N:8]([C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 137332146,8-Difluoro-1,4-dihydro-4-oxo-1-(4-fluorophenyl)-7-(1-pyrrolidinyl)-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.37 g of 6,7,8-trifluoro-1,4-dihydro-4-oxo-1-(4-fluorophenyl)-quinoline-3-carboxylic acid are refluxed with 2.3 g of pyrrolidine in 30 ml of absolute pyridine for 6 hours. The solvent is distilled off in vacuo, the residue is suspended in 50 ml of ice-water, the pH is brought to 1-2 with hydrochloric acid and the precipitate is filtered off with suction, washed with water and dried. 2.5 g of (I) ##STR41## of melting point 282°-284° C. are obtained. Recrystallization from glycol monomethyl ether/ethanol.

Workup

  1. distillationThe solvent is distilled off in vacuo
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with water
  4. customdried
  5. customof melting point 282°-284° C. are obtained
  6. customRecrystallization from glycol monomethyl ether/ethanol

Sources & evidence

ORD record
ord-d017b4df01404950942e218e1bbde3fd
Source dataset
uspto-grants-1991_01
Patent number
US04981854

Reaction notes

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