Maleic Anhydride → HCID 22222645, compound

HRID 1468574Notes

Reaction equation

HRID 1468574 reaction equation
C1(=O)[O:6][C:4](=[O:5])C=C1.N[C:9]1[CH:14]=[CH:13][C:12](/[C:15](=[CH:19]/[C:20]([NH2:22])=[O:21])/[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1>C(Cl)(Cl)Cl>[C:4]([C:9]1[CH:14]=[CH:13][C:12](/[C:15](=[CH:19]/[C:20]([NH2:22])=[O:21])/[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 67321915HCID 67321915, compound

Product 1

HCID 22222645HCID 22222645, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of maleic anhydride (5.0 g. 50.9 mmol) in chloroform (100 ml) was added p-aminophenyl maleamic acid (6.99 g, 50.9 mmol). The resulting mixture was heated to reflux for 3 h. The solution was then cooled and a precipitate formed. The precipitate was filtered, washed with ethyl acetate and dried, to give 2N-(4-carboxyphenyl)maleamic acid (99%) as a solid.14 mp: 218-220° C. 1H NMR (DMSO-d6): δ 6.30 (d, J=12.0 Hz, 1H), 6.47 (d, J=1.20 Hz, 1H), 7.71 (d, J=8.4 Hz, 2H), 7.88 (d, J=8.8 Hz, 2H), 10.59 (s, 1H), 12.83 (brs, 1H); HRMS (m/z): [M−H]− calcd for C11H8NO5, 234.0408; found, 234.0406.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 h
  3. temperatureThe solution was then cooled
  4. customa precipitate formed
  5. filtrationThe precipitate was filtered
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-d259d3ac73d346e5b37e44918a21154c
Source dataset
uspto-grants-2015_04
Patent number
US09005670B2

Reaction notes

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