Hydrochloric Acid → 5-bromo-2-formyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

Participants

Reaction Steps

Step 2 A suspension of 5-bromo-N2-methoxy-N2-methyl-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide (1.73 g, 4.55 mmol) in THF (40 mL) was treated with lithium aluminum hydride (0.259 g, 6.82 mmol) portionwise over 30 min at 0° C. After 20 min, more lithium aluminum hydride (120 mg) was added portionwise, and the mixture was stirred at rt for 20 min. The reaction mixture was cooled to 0° C. and treated dropwise with 0.5 M hydrochloric acid, and the resulting mixture was extracted three times with DCM. The combined organic phases were washed with NaHCO3 (aq) and water, dried and concentrated to provide 5-bromo-2-formyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a yellow solid (1.31 g, 90%), used without further purification. Mass spectrum m/z 321, 323 (M+H)+.

Provenance & Evidence