4-Chloroaniline → AF-794/00086051

HRID 1784041Notes

Reaction equation

HRID 1784041 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1>C(#N)C>[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:1](/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])=[O:7])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 7923Maleic Anhydride

Product 1

HCID 5356193AF-794/00086051Yield 97.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 29.3 g (300 mmol) of maleic anhydride in 500 ml of acetonitrile was treated portionwise with 40 g (310 mmol) of 4-chloroaniline and stirred at room temperature during 24 hrs. The thick precipitate that had formed was filtered off, washed with cold acetonitrile and dried i.v. to yield 65.7 g (97%)of the title compound. Yellow solid. MS: 226 (M+H)+.

Workup

  1. customThe thick precipitate that had formed
  2. filtrationwas filtered off
  3. washwashed with cold acetonitrile
  4. customdried i.v

Sources & evidence

ORD record
ord-ebd3d6c044f84cc9a66afcd766b68400
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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