Sodium Azide → Racemic 6-azido-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Participants

Reaction Steps

To a solution of racemic 6-bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (100 mg, 0.4 mmol) in DMF (2611 mL) and acetic acid (65.3 mL) was added a solution of sodium azide (52.0 mg, 0.8 mmol) in water (522 mL) dropwise at 0° C. After 1 hour, the reaction was complete. The mixture was directly loaded to a 24 g ISCO column and purified by ISCO Combiflash Companion (0% ethyl acetate-hexane for 3 min then ramped to 20% ethyl acetate-hexane over 7 min then 20% ethyl acetate-hexane for 5 more minutes. The product came out 8-10 min) to afford racemic 6-azido-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (35 mg, 0.16 mmol, 41.2%) as a white solid: LCMS=213.22 [M+H]+.

Provenance & Evidence