Phenylacetonitrile → 3-(2-Methyl-pyridin-4-yl)-3-oxo-2-phenyl-propionitrile

HRID 1097858Notes

Reaction equation

HRID 1097858 reaction equation
CCC([O-])(C)C.[K+].[C:8]1([CH2:14][C:15]#[N:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O:19][C:20](=O)[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=1)C>C1COCC1>[CH3:27][C:23]1[CH:22]=[C:21]([C:20](=[O:19])[CH:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]#[N:16])[CH:26]=[CH:25][N:24]=1

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 12243767Ethyl 2-methylisonicotinateHCID 23683543Potassium t-amylate

Product 1

HCID 574213293-(2-Methyl-pyridin-4-yl)-3-oxo-2-phenyl-propionitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-pentylate (25% in toluene, 11.3 mL, 20 mmol) was added dropwise to a solution of phenylacteonitrile (590 mg, 5.0 mmol, [CAS Reg. No. 140-29-4]) in THF (8 mL). After 45 min, 2-methyl-isonicotinic acid ethyl ester (998 mg, 6.0 mmol, [CAS Reg. No. 25635-17-0]) was added drop wise, and the mixture was stirred for 3 h at r.t. The solvent was evaporated, and the residue was taken up in ethyl acetate, and washed with 1N aqueous HCl. The combined water layers were saturated with NaCl, and the crude title compound (as an orange precipitate) was collected by filtration. Evaporation of the organic layer gave an additional small crop of crude product. The combined material (1.02 g, 85%) was used in the next step without further purification. 1H NMR (300 MHz, DMSO-D6) □ 8.81 (1H, d), 7.94 (1H, s), 7.86 (1H, d), 7.78 (2H, d), 7.44 (2H, dd), 7.33 (1H, d), 2.71 (3H, s); MS (m/e)=237.1 [MH+].

Workup

  1. addition25635-17-0]) was added drop wise
  2. customThe solvent was evaporated
  3. washwashed with 1N aqueous HCl
  4. filtrationthe crude title compound (as an orange precipitate) was collected by filtration
  5. customEvaporation of the organic layer
  6. customgave an additional small crop of crude product
  7. customThe combined material (1.02 g, 85%) was used in the next step without further purification

Sources & evidence

ORD record
ord-fb9e5eaa12544b3b9fc75cce3ccb0982
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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