Lithium hydroxide, monohydrate → N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-malonamic acid

HRID 1665661Notes

Reaction equation

HRID 1665661 reaction equation
O[Li].O.C([O:6][C:7](=[O:25])[CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]2=[O:24])=[CH:14][CH:13]=1)=[O:10])C>CO.C1COCC1.O>[O:24]=[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]1[C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:7]([OH:25])=[O:6])=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57875799N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-malonamic acid ethyl ester

Product 1

HCID 57875822N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-malonamic acidYield 95.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (56 mg, 1.3 mmol) was added to a solution of N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-malonamic acid ethyl ester (200 mg, 0.6 mmol) in methanol (0.5 mL), THF (1 mL) and H2O (0.5 mL) and the resulting mixture was stirred for 1 hour at room temperature then concentrated. The residue was diluted with water and acidified with concentrated HCl. The resulting precipitate was isolated by filtration to afford 156 mg (86%) of N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-malonamic acid. 1H NMR: (DMSO-d6): δ 12.8 (s, 1H), 10.3 (s, 1H), 7.78-7.6 (m, 3H), 7.5 (t, 1H), 7.4-7.3 (m, 2H), 6.5 (d, 1H), 6.38 (t, 1H), 3.4 (d, 2H).

Workup

  1. concentrationthen concentrated
  2. additionThe residue was diluted with water
  3. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-dd04ca5b04714475baa8cc9bd4a9b917
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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