Ethanol → 6-Methyl-2-oxo-1-phenyl-1,2-dihydro-pyridine-3-carboxylic acid

HRID 1662028Notes

Reaction equation

HRID 1662028 reaction equation
[O-]CC.[Na+].CCO.[O:8]=[C:9]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:10][C:11]([O:13]CC)=[O:12].CO/[CH:25]=[CH:26]/[C:27](=O)[CH3:28]>>[CH3:25][C:26]1[N:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:9](=[O:8])[C:10]([C:11]([OH:13])=[O:12])=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 639675(3E)-4-Methoxy-3-buten-2-oneHCID 2723922Sodium ethoxideHCID 3016808Propanoic acid, 3-oxo-3-(phenylamino)-, ethyl ester

Product 1

HCID 179666306-Methyl-2-oxo-1-phenyl-1,2-dihydro-pyridine-3-carboxylic acidYield 27.1%

Procedure

To a solution of sodium ethoxide in EtOH (prepared from sodium (0.5 g, 21.75 mmol) dissolved in EtOH (40 mL)) is added ethyl 3-oxo-3-(phenylamino)propanoate (4 g, 19.30 mmol) and trans-4-methoxy-3-buten-2-one (2 g, 19.98 mmol). After the reaction is stirred at reflux overnight, the mixture is concentrated. The residue is partitioned between H2O (50 mL) and EtOAc (50 mL). The aqueous layer is acidified with concentrated HCl to a pH 3˜4 and then it is extracted with EtOAc. The organic extracts are dried and concentrated. The residue is purified by silica gel column chromatography eluting with DCM:MeOH (25:1) to give the product (1.20 g, 27% yield). MS (m/z): 230.0 (M+H).

Workup

  1. temperatureat reflux overnight
  2. concentrationthe mixture is concentrated
  3. customThe residue is partitioned between H2O (50 mL) and EtOAc (50 mL)
  4. extractionit is extracted with EtOAc
  5. customThe organic extracts are dried
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting with DCM:MeOH (25:1)

Sources & evidence

ORD record
ord-838fd51214004514a97fb19e5d728dfe
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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