Triethylamine → HCID 178426651, compound

Reaction equation

[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:11].Cl.[NH2:13][OH:14].C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:6]([NH:13][OH:14])=[NH:7])=[CH:8][C:9]=1[CH3:10]

Participants

Procedure

A mixture of 4-bromo-3,5-dimethyl-benzonitrile (1.50 g), hydroxylamine hydrochloride (0.90 g), triethylamine (1.8 mL) and ethanol (30 mL) is stirred at reflux temperature for 4 h. After cooling to room temperature, the mixture is concentrated, the residue is taken up in water, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 7:3→3:7) to give the title compound. LC (method 11): tR=0.73 min; Mass spectrum (ESI+): m/z=243/245 (Br) [M+H]+.