Hydrochloric Acid → HCID 84740169, compound

Participants

Reaction Steps

HCl (g) was bubbled through a solution of (4,6-dimethyl-1H-indol-3-yl)acetonitrile from Step B (83.0 mg, 0.450 mmol) in MeOH (5 mL). The reaction mixture was stirred for 30 min, then H2O (1 mL) was added and stirring was continued for 2 h. The MeOH was removed under vacuum and the reaction mixture was extracted with EtOAc (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was dissolved in MeOH (2 mL) containing a drop of conc. H2SO4 and the resulting mixture was stirred for 16 h. The reaction mixture was partitioned between EtOAc (10 mL) and saturated NaCl (5 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the crude product by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 80:20, gave the title compound. MS: m/z=218 (M+1).

Provenance & Evidence