Water → N-(6-phenyl-pyridin-3-yl)-malonamic acid

HRID 1665650Notes

Reaction equation

HRID 1665650 reaction equation
O[Li].O.C([O:6][C:7](=[O:24])[CH2:8][C:9]([NH:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)=[O:10])C.C1COCC1.O>CO>[C:18]1([C:15]2[N:14]=[CH:13][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:7]([OH:24])=[O:6])=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57875819N-(6-phenyl-pyridin-3-yl)-malonamic acid ethyl ester

Product 1

HCID 57874490N-(6-phenyl-pyridin-3-yl)-malonamic acidYield 57.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiOH.H2O (11 mg, 0.26 mmol) was added to a solution of N-(6-phenyl-pyridin-3-yl)-malonamic acid ethyl ester (50 mg, 0.17 mmol) in a mixture of methanol (0.5 mL), THF (1 mL) and H2O (0.3 mL). The reaction mixture was stirred for 1 hour at room temperature then concentrated. The residue was diluted with water, acidified with concentrated HCl and the resulting precipitate was filtered to afford 25 mg (44%) of N-(6-phenyl-pyridin-3-yl)-malonamic acid. LCMS: 257.09 (M+1)+, 96%, 1H NMR: (DMSO-d6): δ 10.5 (s, 1H), 8.8 (d, 1H), 8.2 (dd, 1H), 8.0 (d, 2H), 7.9 (d, 1H), 7.5-7.3 (m, 3H), 3.4 (s, 2H).

Workup

  1. concentrationthen concentrated
  2. additionThe residue was diluted with water
  3. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-701e30b130a448928fc7f789e0643441
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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