Sodium Hydroxide → N-(3-phenyl-isoxazol-5-yl)-malonamic acid

HRID 1665682Notes

Reaction equation

HRID 1665682 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:22])[CH2:7][C:8]([NH:10][C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=1)=[O:9])C>C1COCC1.O>[C:16]1([C:13]2[CH:12]=[C:11]([NH:10][C:8](=[O:9])[CH2:7][C:6]([OH:22])=[O:5])[O:15][N:14]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57875820N-(3-phenyl-isoxazol-5-yl)-malonamic acid ethyl ester

Product 1

HCID 57875817N-(3-phenyl-isoxazol-5-yl)-malonamic acidYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (57 mg, 1.4 mmol) was added to a stirred solution of N-(3-phenyl-isoxazol-5-yl)-malonamic acid ethyl ester (78 mg, 0.28 mmol) in a mixture of THF (12 mL) and H2O (12 mL) and stirring was continued at ambient temperature overnight. The reaction mixture was concentrated. The residue was diluted with water, washed with diethyl ether, acidified with concentrated HCl. The precipitate was filtered to afford 45 mg (64.28% Yield) of N-(3-phenyl-isoxazol-5-yl)-malonamic acid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with water
  3. washwashed with diethyl ether
  4. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-b2c7b3e1e0c74e5d9926245c2ec3be91
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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