Potassium Hydroxide → [9-(2,5-dichlorobenzyl)-9H-beta-carbolin-3-yl]methylamine

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Reaction Steps

This formamide (2.90 g, 7.5 mmol) was treated with potassium hydroxide (5.40 g, 9.4 mmol) in ethanol/water (5:1, 48 mL) at reflux for 6 hours. The resulting suspension was cooled to room temperature, concentrated, and diluted with CH2Cl2 (50 mL). The organic phase was washed with water (2×25 mL), dried (Na2SO4), filtered and concentrated to give [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methylamine as a yellow solid. The crude material was recrystallized from ethyl acetate/hexane to give 1.48 grams (55%) of a pale-yellow solid. 1H NMR (CDCl3) δ8.70 (s, 1H), 8.18 (d,J=7.9 Hz, 1H), 8.03 (s, 1H), 7.58 (td,J=7.2, 1.1 Hz, 1H) 7.32-7.42 (6-line m, 3H), 7.20 (dd, J=9.6, 2.6 Hz, 1H), 6.55 (d, J=2.6 Hz, 1H), 5.60 (s, 2H), 4.28 (d, 1H), 1.96 (br s, 2H); MS monoisotopic mass (calculated) 355.1, MH+ (observed) 356.7.

Provenance & Evidence