Oxalyl chloride → 4,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

Participants

Reaction Steps

3,5-Dimethoxyaniline hydrochloride (80.21 g, 0.424 mol) was added cautiously to oxalyl chloride (136 ml, 1.56 mol) and the solution heated at reflux for 3 hours. The solution was cooled and concentrated in vacuo. Methanol (300 ml) was added to the residue and the mixture heated at reflux for 1 hour. The reaction was allowed to cool, and the resulting precipitate filtered and washed with methanol to yield 4,6-dimethoxyisatin (40.4 g, 46%) as a yellow solid.

Provenance & Evidence