Ammonia → (5Z)-N-Hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-5-imine

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Reaction Steps

In a 100-mL, 3N round-bottomed flask 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one (2.0 g, 1.0 eq.) was dissolved in EtOH (24.0 mL) and H2O (6.0 mL) at RT. Then Sodium acetate trihydrate (8.175 g, 4.0 eq.) and Hydroxylamine hydrochloride (4.174 g, 4.0 eq.) were added at the same temperature. The progress of the reaction was followed by TLC analysis on TLC with 5% Methanol: dichloromethane with ammonia atmosphere as mobile phase and visualization with U.V light. The reaction mixture was quenched in 50 mL water and extracted by dichloromethane. Organic layer was concentrated by rotary evaporation (35° C., 20 mmHg) to afford 2.10 g of crude compound which was used in the next step without purification.

Provenance & Evidence