1-Nitropropane → HCID 22638762, compound

Participants

Reaction Steps

In 5 mL of acetic acid were combined the crude 6-(2-dimethylaminomethyl-cyclo-propyl)-1H-indole-3-carbaldehyde, ammonium hydrogen phosphate (0.99 g, 7.50 mmol), and nitropropane (0.09 g, 1.03 mmol.). The mixture was stirred and heated to a gentle reflux for 16 h. Water was added after cooling reaction to room temperature, and the mixture was made basic by the addition of 1 N NaOH. The mixture was extracted with methylene chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give a brown oil. The oil was purified by flash chromatography (50% methanol/ethyl acetate) to give 6-(2-dimethylaminomethyl-cyclopropyl)-1H-indole-3-carbonitrile as an amber oil (93 mg, 38%). 1H NMR (CDCl3): δ7.58 (m, 2H), 6.99 (m, 2H), 5.75 (s, 1H), 2.46 (m, 1H), 2.33 (s, 7H), 1.89 (m, 1H), 1.20 (m, 1H), 0.98 (m, 1H), 0.86 (m, 1H); FIMS: 238.2 (M−H); LCMS: 72% AP.

Provenance & Evidence