3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). 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 remove the solvents under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine 2-chloro-2-propenenitrile (3.0 g, 34.3 mmol), 2-aminophenol (3.27 g, 29.96 mmol), acetone (50 mL), and potassium chloride (5 g, 36.18 mmol). Stir the mixture at ambient temperature for 16 hours. Filter the mixture and wash the filter cake with EtOAc. Concentrate the filtrate under reduced pressure to give a residue. Purify via flash column chromatography using a gradient of 1-50% EtOAc in petroleum ether to elute. Combine the product fractions and remove solvents under reduced pressure to provide the title compound (1.5 g, 21.6%). MS (m/z): 161 (M+1). Filter the mixture wash the filter cake with EtOAc Concentrate the filtrate under reduced pressure to give a residue Purify via flash column chromatography to elute Combine the product fractions and remove solvents under reduced pressure