4-Methylmorpholine → 4'-Methyl-[1,1'-biphenyl]-4-carbohydrazide

Participants

Reaction Steps

To a stirring solution of 4′-methyl-[1,1′-biphenyl]-4-carboxylic acid (240 mg, 1.13 mmol) and 4-methylmorpholine (131 μL, 1.19 mmol) in THF (3 mL) was added isobutyl chloroformate (147 μL, 1.13 mmol). After 1 h the reaction mixture was added through a syringe filter to a stirring solution of hydrazine (1.24 mL, 1.24 mmol, 1 M in THF) in THF (1 mL). After stirring a further 30 min at room temperature, the reaction mixture was poured into NaHCO3 (20 mL) and extracted with DCM (3×20 mL). The combined organic extracts were dried over MgSO4 and evaporated. The crude product was purified by column chromatography (MeOH/DCM) to give 152 mg (59%) of 4′-methyl-[1,1′-biphenyl]-4-carbohydrazide INT-50 as a white solid. LCMS-ESI (m/z) calculated for C14H14N2O: 226; found 227 [M+H]+, tR=1.62 min (Method 10).

Provenance & Evidence