N-(4-aminophenyl)butanamide

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

Procedure: To a solution of 1,4-phenylenediamine (0.5 g, 4.62 mmol) in anhydrous CH2Cl2 (15 mL) was added NMM (0.51 mL, 4.62 mmol). To the resulting mixture was added dropwise butyryl chloride (0.45 mL, 4.62 mmol) in anhydrous CH2Cl2 (5 mL) at 0° C., and stirred for 0.5 h. The reaction mixture was extracted with CH2Cl2 (20 mL) and washed with H2O (20 mL). The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography over silica gel (EtOAc:hexane=1:3) to give N-(4-aminophenyl)butyramide (KYJ3-006-2, 0.31 g, 36%) as a colorless oil. The reaction mixture was extracted with CH2Cl2 (20 mL) washed with H2O (20 mL) The organic layer was dried over MgSO4 evaporated in vacuo The residue was purified by column chromatography over silica gel (EtOAc:hexane=1:3)