Hydrogen Bromide → 7-Bromoacetyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
Reaction equation
[C:1]([C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:20])[C:9]([C:17]([OH:19])=[O:18])=[CH:10][N:11]2[CH2:15][CH3:16])=[CH:6][C:5]=1[F:21])(=[O:3])[CH3:2].[Br:22]([O-])(=O)=O.[K+].Br>C(O)(=O)C>[Br:22][CH2:2][C:1]([C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:20])[C:9]([C:17]([OH:19])=[O:18])=[CH:10][N:11]2[CH2:15][CH3:16])=[CH:6][C:5]=1[F:21])=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To 1.12 g (3.80 mmol) of the 7-acetyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 30 ml of acetic acid was added 0.18 g of potassium bromate and 1.48 ml of 48% hydrobromic acid. The mixture was stirred at 50° C. for 24 hours. The mixture was concentrated to one-half volume and 20 ml of water was added. The solids were filtered to give 1.3 g of the 7-bromoacetyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 213°-215° C.
Workup
- concentrationThe mixture was concentrated to one-half volume and 20 ml of water
- additionwas added
- filtrationThe solids were filtered
Sources & evidence
- ORD record
- ord-6e5cc58fd6724fa89bcb1665a24302bd
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04665079
Reaction notes
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