Nitric Acid → 2-Nitro-3,6-bis(trifluoromethyl)benzenamine
Reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[F:10][C:11]([F:24])([F:23])[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[NH2:22].[OH-].[Na+]>>[N+:1]([C:14]1[C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=[C:12]([C:11]([F:10])([F:23])[F:24])[C:13]=1[NH2:22])([O-:4])=[O:2]Participants
5
Procedure
Nitric acid (7 mL) was added to sulfuric acid (10 mL) cautiously at 0° C. 2,5-Bis(trifluoromethyl)benzenamine (2 g, 8.7 mmol) was added in small portions at 0° C. over 20 minutes and the resulting slurry was stirred at 0° C. to room temperature for 3 hours. The mixture was poured into ice water (100 mL) and basified with sodium hydroxide solution, and extracted with EtOAc (80 mL×3). The combined organic layers were washed with brine (80 mL), dried over sodium sulfate, filtered and concentrated to give a crude product of 2-nitro-3,6-bis(trifluoromethyl)benzenamine (containing isomers) which was used in the next step without further purification (2.3 g). MS (ESI): m/z 275 [M+H]+
Workup
- extractionextracted with EtOAc (80 mL×3)
- washThe combined organic layers were washed with brine (80 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3eda407e608b4199880f24b3c184d53b
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969349B2
Reaction notes
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