Acetic Anhydride → N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

Ac2O (44.6 mL, 473 mmol) was added dropwise to a stirred solution of 5-indanamine (1) (30 g, 225 mmol) in dioxane (120 mL) at 0° C. and the solution stirred at 20° C. for 48 h. The solution was diluted with water (500 mL), stirred 20 min and the precipitate filtered. The solid was washed with water (3×30 mL) and air-dried to give acetamide 16 (37.4 g, 95%) as a tan solid: mp 99-101° C.; 1H NMR δ 7.38-7.43 (m, 2H, H-4, NH), 7.10-7.16 (m, 2H, H-6, H-7), 2.85 (br q, J=7.7 Hz, 4H, H-1, H-3), 2.13 (s, 3H, CH3), 2.06 (br, p, J=7.4 Hz, 2H, H-2); 13C NMR δ 168.3, 145.1, 140.3, 136.0, 124.4, 118.2, 116.6, 33.0, 32.3, 25.6, 24.4.

Provenance & Evidence