1-Fluoro-2-nitrobenzene → Benzenamine, N-methyl-2-nitro-
Reaction equation
Cl.[CH3:2][NH2:3].[Na].F[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]>C1COCC1>[CH3:2][NH:3][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Methylamine hydrochloride (2.7 g) and a 10% aqueous solution of sodium hydroxyde (30 ml) were added to a solution of 1-fluoro-2-nitrobenzene (2.82 g) in THF (20 ml). The mixture was kept at 23° for 24 h. The reaction mixture was then concentrated in vacuo, taken up with 10% aqueous sodium hydroxide (30 ml) and extracted with EA (3×30 ml). The combined organic layers were washed with a saturated ammonium chloride solution (50 ml), brine (50 ml) and dried. Evaporation of the solvent gave the title compound as an orange oil (2.894 g).
Workup
- concentrationThe reaction mixture was then concentrated in vacuo
- extractionextracted with EA (3×30 ml)
- washThe combined organic layers were washed with a saturated ammonium chloride solution (50 ml), brine (50 ml)
- customdried
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-fe1565a7fa9242fab8b27da25e0bd0c6
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05686449
Reaction notes
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