Hydrochloric Acid → 2,3-Dimethyl-6-nitrobenzylamine
Reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]#[N:5].Cl>O1CCCC1>[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[CH2:4][NH2:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of borane-tetrahydrofuran complex (94.6 g, 1.1 mole) in tetrahydrofuran (1100 mL) was added dropwise to a stirred solution of 2,3-dimethyl-6-nitrobenzonitrile (96 g, 0.55 mole) in dry tetrahydrofuran (650 mL) maintained under an atmosphere of argon. After stirring overnight, 10% hydrochloric acid solution (1300 mL) was added dropwise and the mixture heated to reflux. After 30 minutes, the tetrahydrofuran was distilled off, the residue filtered to remove insoluble material and the filtrate made basic with concentrated ammonium hydroxide solution (350 mL). The mixture was extracted with diethyl ether (2×500 mL), the combined extracts washed with water (2×400 mL), dried over potassium carbonate and concentrated to afford 2,3-dimethyl-6-nitrobenzyl amine (93.85 g, 95%) as an oil used without further purification as follows.