Ammonia → 1-(2-Hydroxyethyl)-2,3-dihydro-1H-indol-4-ol

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Reaction Steps

1.9 g of sodium cyanoborohydride were added to a solution of 8.85 g of 4-hydroxy-1-N-(β-hydroxyethyl)indole, obtained in the preceding stage, in 40 cm3 of acetic acid, the temperature being maintained below 30° C. After stirring for 30 minutes, the reaction mixture was poured onto 200 g of ice-cold water and the pH was neutralized to 7.5 by addition of 30% aqueous ammonia. The precipitate obtained was filtered off and dried. 7.75 g of 4-hydroxy-1-N-(β-hydroxyethyl)indoline were obtained, the melting point of which was 108° C. 13C and proton nuclear magnetic resonance (N.M.R.) analysis of the product obtained was found to be in accordance with the expected product.

Provenance & Evidence