1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester → HCID 53739370, compound

HRID 1382219Notes

Reaction equation

HRID 1382219 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[NH:23]1[CH2:29][CH2:28][CH2:27][C@H:24]1[CH2:25][OH:26]>CN1CCCC1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:23]4[CH2:29][CH2:28][CH2:27][C@H:24]4[CH2:25][OH:26])[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 640091L-Prolinol

Product 1

HCID 53739370HCID 53739370, compound

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

A solution of 3.1 g (0.01 mmol) of ethyl 1-cyclopropyl-1,4-dihydro-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate and 3.03 g (0.03 mmol) of L-prolinol in 15 ml of N-methylpyrrolidine was stirred at 80° C. for 2.5 hours. The solvent was removed by distillation under reduced pressure and the oily residue was recrystallized from ethyl acetate/ether. The resulting ester was saponified analogously to Example 1A. There was obtained 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[(S)-2-hydroxymethyl-1-pyrrolidinyl]-4-oxoquinoline-3-carboxylic acid, m.p. 209°-210° C.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. customthe oily residue was recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-66ebf989a25a435d9e145572c8d937ab
Source dataset
uspto-grants-1989_02
Patent number
US04806541

Reaction notes

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