Sulfuric Acid → 2-Amino-5-nitro-4-trifluoromethyl-benzoic acid
Reaction equation
C([NH:4][C:5]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[C:11]([N+:18]([O-:20])=[O:19])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C.OS(O)(=O)=O.[OH-].[Na+]>CO.O>[NH2:4][C:5]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[C:11]([N+:18]([O-:20])=[O:19])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 49.5 g (169 mmol) of 2-acetylamino-5-nitro-4-trifluoromethyl-benzoic acid in 600 ml of methanol and 100 ml of water is cooled to 0° C. and 71.1 ml (1.33 mol) of concentrated H2SO4 are added dropwise. Upon completion of the addition, the mixture is heated to reflux for 1 hour. The mixture is then cooled to 0° C., the pH is adjusted to 10 with a 30% aqueous NaOH-solution and it is stirred for 1 hour. The methanol is distilled off and the remaining aqueous solution is diluted with water and extracted with t-butyl methylether. The aqueous phase is acidified with concentrated HCl-solution and the resulting yellow suspension is filtered and washed with water. The solid is dried in vacuo at 100° C. to give 28.3 g (67%) of 2-amino-5-nitro-4-trifluoromethyl-benzoic acid, m.p. 237° C.
Workup
- additionUpon completion of the addition
- temperaturethe mixture is heated
- temperatureto reflux for 1 hour
- distillationThe methanol is distilled off
- additionthe remaining aqueous solution is diluted with water
- extractionextracted with t-butyl methylether
- filtrationthe resulting yellow suspension is filtered
- washwashed with water
- customThe solid is dried in vacuo at 100° C.
Sources & evidence
- ORD record
- ord-feba52758ed3441bb927c40b364f13df
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299085B2
Reaction notes
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