1,2,3,4-Tetrahydroquinoline → 1,2,3,4-Tetrahydro-1-nitrosoquinoline

Participants

Reaction Conditions

Reaction Steps

1,2,3,4-Tetrahydroquinoline (10 g, 75 mmol) was dissolved in 3N HCl (50 mL) at 0° C. The reaction mixture was stirred for 5 min. at 0° C., then a solution of sodium nitrite (6.22 g, 90 mmol) in water was added at 0° C., and the mixture stirred for 2 h at RT. After completion of reaction, water was added and the mixture extracted with EtOAc (2×200 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated under vacuum to obtain 10 g of product.

Provenance & Evidence