Sodium Hydroxide → HCID 19744368, compound

Participants

Reaction Steps

1.9 g. of phosphorus oxychloride was slowly added to 1.48 g. of N,N-dimethylacetamide at 0° C. The mixture was allowed to attain room temperature and a solution of 1.0 g. 6-(2-ethylhexanamido)indole in 2 ml. N,N-dimethylacetamide was added. After 15 minutes the reaction solution was basified to pH 14 with 20% w/v sodium hydroxide solution, briefly heated under reflux, then cooled and extracted with ethyl acetate. The combined extracts were washed with water, then with brine, dried (MgSO4) and evaporated to give 0.93 g (80%) of 3-acetyl-6-(2-ethylhexanamido)indole (DD) as an orange powder; partial NMR: 2.5 (s, 3H), COCH3), 7.7 (d, 1H, H2 -indole), 9.8 (br, s, 1H, NH).

Provenance & Evidence