Water → 7-Chloro-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2302228Notes

Reaction equation

HRID 2302228 reaction equation
[Cl:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19]CC)=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:23].O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:23]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 23431783Ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 153471917-Chloro-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

33.8 g (0.1 mol) of ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate are heated under reflux for 3 hours in a mixture of 100 ml of acetic acid, 20 ml of water and 10 ml of concentrated sulphuric acid. After cooling, the mixture is poured onto 100 ml of ice water, and the deposited precipitate is filtered off with suction, washed with water and ethanol and dried in vacuo at 60° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe deposited precipitate is filtered off with suction
  3. washwashed with water and ethanol
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-76016484c3e64cf891eb4c4e2b74b408
Source dataset
uspto-grants-2002_08
Patent number
US06432948B1

Reaction notes

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