Maleic Anhydride → (Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid

HRID 1478095Notes

Reaction equation

HRID 1478095 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([NH:11]N)=[O:10])[CH:6]=[CH:5][N:4]=1.[O:13]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]1=[O:19]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([NH:11][C:17](=[O:18])/[CH:16]=[CH:15]\[C:14]([OH:19])=[O:13])=[O:10])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 3225512-Methoxyisonicotinohydrazide

Product 1

HCID 67958827(Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 8 (167 mg, 1.0 mmol) in 10 mL of THF was added furan-2,5-dione (110 mg, 1.1 mmol). The mixture was stirred at ambient temperature for 2 hours. After removal of the solvent, the residue was diluted with 10 mL of dichloromethane. The solid was collected by filtration to give (Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid 9 as a solid.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted with 10 mL of dichloromethane
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-9b7f6c352d4f420d8d1489f15ee61bf6
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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