Maleic Anhydride → Maleic acid anilide

HRID 2073338Notes

Reaction equation

HRID 2073338 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:11]2CC[C:10]=12>C(Cl)Cl>[C:9]1([NH:8][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])[CH:16]=[CH:15][CH:14]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 53748840HCID 53748840, compound

Product 1

HCID 1550938Maleic acid anilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

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.

Workup

  1. customImmmediately, bright yellow precipitates
  2. customformed quantitatively
  3. filtrationThe reaction mixture was filtered
  4. customthe yellow solid product collected
  5. washwas washed with methylene chloride (3 ×25 ml)
  6. customair-dried

Sources & evidence

ORD record
ord-f806ca383b3a48b899e90125da6bfef5
Source dataset
uspto-grants-1990_04
Patent number
US04916235

Reaction notes

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