反应详情

Add hydroxylamine hydrochloride (2.87 g, 41.37 mmol) and ammonium acetate (4.78 g, 62.06 mmol) to a solution of indole-7-carboxaldehyde (3.0 g, 20.68 mmol) in ethanol: H2O (3:1) (120 ml). Stir at room temperature for 2 hours. Add ammonium hydroxide (25 ml, 0.72 mmol) and zinc (11.0 g, 8.1 mmol) in portions. Filter the reaction mixture, dilute with ethyl acetate, and wash with water. Extract the organic layer with 1N HCl. Make the aqueous layer basic by adding 1N NaOH and extract with ethyl acetate. Wash the organic layer with water followed by saturated aqueous sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure to provide the desired compound (2.69 g, 89%) as a white solid.

1. filtrationFilter the reaction mixture
2. additiondilute with ethyl acetate
3. washwash with water
4. extractionExtract the organic layer with 1N HCl
5. additionby adding 1N NaOH
6. extractionextract with ethyl acetate
7. washWash the organic layer with water
8. dry with materialdry over magnesium sulfate
9. concentrationconcentrate under reduced pressure