3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile → 1-(3,4-Dihydro-2H-1,4-benzoxazin-2-yl)methanamine

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Reaction Steps

Add 3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile (600 mg, 3.75 mmol) to THF (20 mL) and then slowly add lithium aluminum hydride (1.0 M in THF; 1 mL, 1.0 mmol). Stir the mixture at ambient temperature for 30 minutes. Add H2O (1 mL) to quench the reaction; filter; and wash the filter cake with EtOAc. Dry the filtrate over Na2SO4; filter; and concentrate the filtrate under reduced pressure to afford a residue. Purify the resulting compound via flash column chromatography using a gradient of 20-50% of MeOH in DCM. Combine the desired fractions and remove the solvents under reduced pressure to provide the title compound as a white solid (390 mg, 63.1%). MS (m/z): 165 (M+1).

Provenance & Evidence