6-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman → 6-Amino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

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Reaction Steps

Solution of 14 (0.114 g, 0.32 mmol) in 5 ml of 4N H2SO4 and 5 ml of methanol was heated to reflux. After refluxing for 15 hours, the methanol was removed under reduced pressure. The remaining aqueous solution was neutralized with NaHCO3 to pH 9, followed by extraction with ethyl acetate three times. The combined organic phase was dried over Na2SO4. Removal of the solvent afforded the desired product 15 (100 mg, 100%) which was used directly for next step.

Provenance & Evidence