Sodium Methoxide → 2-Hydroxybenzo(b)thiophene-3-carboxamide

Reaction equation

[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:13]([NH2:15])=[O:14])[C:9](OC)=[O:10].C[O-].[Na+].C([O-])(=O)CC(N)=O>CN(C)C=O>[OH:10][C:9]1[S:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]=1[C:13]([NH2:15])=[O:14]

Participants

Procedure

Methyl o-mercaptophenylmalonamate (4.5 g, 0.02 m) and dried dimethylformamide (50 ml) at 10° C. is treated with sodium methoxide (3.2 g, 0.06 m) under a nitrogen atmosphere, and the resultant mixture allowed to stir at ambient temperature until no starting malonamate remains (thin-layer analysis). The reaction mixture is added to a stirred excess dilute hydrochloric acid-ice mixture, aged and filtered to yield 2-hydroxybenzo(b)thiophene-3-carboxamide.