Hydrochloric Acid → 3-((1-Ethylpropyl)amino)-6-methyl-2,4-dinitrobenzyl alcohol

Reaction equation

C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[C:8]([NH:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:7]=1[N+:22]([O-:24])=[O:23])(=O)C.Cl.O>CO>[CH2:18]([CH:17]([NH:16][C:8]1[C:7]([N+:22]([O-:24])=[O:23])=[C:6]([C:11]([CH3:12])=[CH:10][C:9]=1[N+:13]([O-:15])=[O:14])[CH2:5][OH:4])[CH2:20][CH3:21])[CH3:19]

Participants

Procedure

A sample of 3-[(1-ethylpropyl)amino]-6-methyl-2,4-dinitrobenzyl acetate (23.1 g; 0.068 mol) is added to a mixture of concentrated hydrochloric acid (30 ml), water (40 ml) and methanol (320 ml). The reaction mixture is refluxed for 4 hours, cooled down and concentrated in vacuo. It is then diluted with water, extracted with ether, and the ether layer dried. The ether is removed in vacuo to leave a red oil, which readily solidifies to a yellow-orange solid (19.9 g; 98.5%). A similarly prepared and purified sample has a melting point of 51°-54° C.