Acetic Acid → 1-Methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 364053Notes

Reaction equation

HRID 364053 reaction equation
CC(C)(OC([CH2:7][NH:8][N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:21])=[C:16]([F:20])[C:17]=2[F:19])[C:12](=[O:22])[C:11]([C:23]([O:25]CC)=[O:24])=[CH:10]1)=O)C.C(O)(=O)C.Cl>O>[F:21][C:15]1[CH:14]=[C:13]2[C:18](=[C:17]([F:19])[C:16]=1[F:20])[N:9]([NH:8][CH3:7])[CH:10]=[C:11]([C:23]([OH:25])=[O:24])[C:12]2=[O:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 137119881-[[(1,1-Dimethylethoxy)carbonyl]methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

Product 1

HCID 135580371-Methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 80.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.00 g (5.0 mmol) of 1-[[(1,1-dimethylethoxy)carbonyl]methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester was added 35 ml of acetic acid and 15 ml of 2N hydrochloric acid. The mixture was placed on a steam bath for 2.5 hours, was diluted with 15 ml of water, and was cooled. The solids were filtered to give 1.09 g of 6,7,8-trifluoro-1,4-dihydro-1-methylamino-4-oxo-3quinolinecarboxylic acid, mp 237°-238° C.

Workup

  1. temperaturewas cooled
  2. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-15193dfb798c4845bb8a3f42610ff3ee
Source dataset
uspto-grants-1986_08
Patent number
US04604401

Reaction notes

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