Methanol → HCID 18671692, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (9H-carbazol-4-yloxy)acetonitrile (1.13 g, 5.1 mmol) in dry THF (50 mL) is added borane-methyl sulfide complex (1.4 mL, 15.3 mmol). The mixture is heated at 85° C. for 6 h. Methanol is added slowly until gas evolution ceased. The solvents are removed under reduced pressure. Methanol (20 mL) is added then removed under reduced pressure. Methanol (50 mL) and concentrated hydrochloric acid are added and the mixture heated at 65° C. overnight. The mixture is neutralized with saturated potassium carbonate and partitioned between water and CH2Cl2. The layers are separated and the organic layer washed twice with water (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography, silica gel (200 mL), using CH3OH/CH2Cl2 (4/96) gave 0.61 g (53%) of the title compound; IR (drift) 3082, 1608, 1585, 1456, 1443, 1346, 1336, 1303, 1252, 1222, 1098, 911, 782, 750, 719 cm−1. 1H NMR (DMSO-d6) δ3.05, 4.13, 6.65, 7.03, 7.12, 7.24, 7.31, 7.41, 8.12; Anal. Calcd for C14H14N2O: C, 74.31; H, 6.24; N, 12.38. Found: C, 73.90; H, 6.32; N, 12.14.

Provenance & Evidence