Maleic Anhydride → Maleic acid anilide

Participants

Reaction Steps

2.80 g (28.55 mmole) of maleic anhydride was dissolved completely in about 60 ml of methylene chloride. To this solution was added the freshly prepared 4-aminobenzocyclobutene (3.35 g., 28.11 mmole). Immmediately, bright yellow precipitates formed quantitatively. The reaction was quite exothermic as evidenced by the self-refluxing of methylene chloride. Additional 30 ml of methylene chloride was added to moderate the reaction temperature. Finally, the resultant bright yellow heterogeneous mixture was stirred overnight at room temperature. The reaction mixture was filtered and the yellow solid product collected was washed with methylene chloride (3 ×25 ml) and air-dried. Yield: 5.03 g (82.4%). Anal Calc. for C12H11NO3 : C, 66.35; H, 5.10; N, 6.45. Found: C, 66.66; H, 5.27; N, 6.34.

Provenance & Evidence