Sodium Hydroxide → Benzoic acid, 2-amino-5-fluoro-3-nitro- (9CI)
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([NH:11]C(=O)C(F)(F)F)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[OH-].[Na+]>C(O)C>[NH2:11][C:5]1[C:4]([N+:18]([O-:20])=[O:19])=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 5-fluoro-3-nitro-2-(2,2,2-trifluoroacetamido)benzoic acid (141; 1.2 g, 4.1 mmol) in ethanol (20 mL) was added 10% aqueous sodium hydroxide solution (20 mL). The resulting reaction mixture was stirred at 80° C. for 3 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting orange solids were acidified with dilute HCl, filtered and dried to afford 2-amino-5-fluoro-3-nitrobenzoic acid 142 (0.73 g, 90%).
Workup
- customThe resulting reaction mixture
- temperatureUpon cooling to room temperature
- concentrationthe reaction mixture was concentrated under reduced pressure
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-f8e421e2af0e40ad88c6ac557de2ea56
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846947B2
Reaction notes
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