Water → 6-Nitro-o-anisidine
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 2-amino-3-nitrophenol (19.25 g) and K2CO3 (19 g) in DMF (100 mL) was added MeI (11 mL) at room temperature and the mixture was stirred over night and then poured into water. The resulting precipitate was collected by filtration and the solid was washed with water to afford the desired product (19 g, 90%). 1H NMR (300 MHz, CDCl3) δ ppm 3.92 (s, 1H), 6.43 (br s, 1H), 6.61 (dd, 1H, J=7.5, 9.0 Hz), 6.89 (dd, 1H, J=0.9, 7.5 Hz), 7.73 (dd, 1H, J=0.9, 9.0 Hz); LC-MS: m/e=169 [M+1]+
Workup
- filtrationThe resulting precipitate was collected by filtration
- washthe solid was washed with water
Sources & evidence
- ORD record
- ord-5902f394338943068ba0956c4d2c0bee
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541411B2
Reaction notes
Loading…