Toluene → N-cyclohexyl-2-nitroaniline
Reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16].C1(C)C=CC=CC=1>ClCCl.CO>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:17])=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
Cyclohexylamine (8.1 ml) was added dropwise to 1-fluoro-2-nitrobenzene (4) (3.7 mg) under a nitrogen atmosphere at 0°. To the resulting orange solid, dry toluene (10 ml) was added and the mixture was stirred at 23 ° C. for 30 min. then diluted with dichloromethane/methanol 1/1 (100 ml) and the organic layer was washed with brine (50 ml), 10 % solution sodium hydroxide (50 ml) and brine (50 ml), dried and concentrated in vacuo to give the title compound as an orange solid (7.45 g). Mp 105°-7° T.l.c. CH-EA (7:3). Rf 0.78
Workup
- washthe organic layer was washed with brine (50 ml), 10 % solution sodium hydroxide (50 ml) and brine (50 ml)
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7dc3ed43c6e84df0846c3d58025e78f4
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05686449
Reaction notes
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