Dimethylacetamide → HCID 59377683, compound

HRID 1691777Notes

Reaction equation

HRID 1691777 reaction equation
[C:1]([N:9]1[CH:14]=[CH:13][C:12](=[O:15])[CH2:11][CH:10]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18](Cl)[CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C2C3C(=CC=CC=3)C=CC=2)C2C(=CC=CC=2)C=CC=1.C(PC(C)(C)C)(C)(C)C.C[C:53]([N:55](C)C)=O>[Zn].[C-]#N.[Zn+2].[C-]#N>[C:1]([N:9]1[CH:14]=[CH:13][C:12](=[O:15])[CH2:11][CH:10]1[C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[C:53]#[N:55])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 31374DimethylacetamideHCID 59377685HCID 59377685, compoundHCID 66906061HCID 66906061, compound

Product 1

HCID 59377683HCID 59377683, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalyst

Conditions

Temperature
90 °C

Procedure

1-Benzoyl-2-(3-chlorophenyl)-2,3-dihydro-pyridin-4-one (910 mg) was placed in an argon filled flask together with 42 mg Pd(II) TFA2, 108 mg binaphthyl-di-tert-butyl phosphine, 39 mg zinc powder, 203.4 mg zinc cyanide and 45 ml dimethylacetamide. The solution was degassed with argon and heated at 90° C. for eight hours. After cooling to room temperature, the mixture was filtered through glass fiber filter paper. The supernatant was basified with ammonium hydroxide and the resulting mixture was extracted with diethyl ether. The combined ether extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography of the residue gave 350 mg 3-(1-benzoyl-4-oxo-1,2,3,4-tetrahydro-pyridin-2-yl)-benzonitrile.

Workup

  1. customThe solution was degassed with argon
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered through glass fiber
  4. filtrationfilter paper
  5. extractionthe resulting mixture was extracted with diethyl ether
  6. dry with materialThe combined ether extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa164b5a6ce44b52b0d2ff1778c1e9c2
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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