Acetic Anhydride → N-[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of crude nitroindanamine 108 (19.82 g, 95.8 mmol) in EtOH (200 mL) and Pd/C (500 mg) was stirred in 2×100 mL batches under H2 (60 psi) for 16 h. The combined batches were filtered through Celite, and washed with warm EtOH (1 L) and then DMF (100 mL). The solvent was evaporated and the residue suspended in dioxane (130 mL), and Ac2O (19 mL, 190 mmol) added dropwise. The mixture was stirred at 20° C. for 16 h, diluted with water (200 mL), the pH adjusted to 10 with cNH3, and the mixture stirred for 30 min. The precipitate was filtered, washed with water (50 mL) and dried to give pure 5-acetamide 109 (15.38 g, 73%) as tan powder: mp 94-96° C.; 1H NMR δ 7.42 (br s, 1H, NH), 7.08-7.14 (m, 3H, H-4, H-6, H-7), 2.97-3.08 (m, 3H, H-2, CH2), 2.78-2.89 (m, 2H, CH2), 2.30 [s, 6H, N(CH3)2], 2.15 (s, 3H, COCH3); 13C NMR δ 168.3, 142.8, 137.9, 136.3, 124.5, 118.5, 116.6, 68.1, 43.8 (2), 37.7, 37.1, 24.5. Anal. calcd for C13H18N2O.H2O: C, 66.1; H, 8.5; N, 11.9. Found: C, 66.1; H, 8.5; N, 11.9%.

Provenance & Evidence