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

HRID 509583Notes

Reaction equation

HRID 509583 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.[C:13]1(=[O:19])[O:18][C:16](=[O:17])[CH:15]=[CH:14]1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([NH:11][C:13](=[O:19])/[CH:14]=[CH:15]\[C:16]([OH:18])=[O:17])=[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 2-methoxypyridine-4-carbohydrazide 8 (167 mg, 1.0 mmol) in 10 mL of THF was added maleic anhydride (110 mg, 1.1 mmol 1). The mixture was stirred at ambient temperature for 2 h. 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. Yield: 190 mg, 71%.

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-fe451837c76a4eb4883fe2b38ec79e89
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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