2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile → 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile

HRID 892521Notes

Reaction equation

HRID 892521 reaction equation
[CH3:1][C:2]1([CH3:20])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:4]=2[O:3]1>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:20])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 156813282,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 150389003,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrileYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.96 g of 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile were dissolved in 100 ml of ethanol and added at room temperature to 100 mg of 10% palladium-on-charcoal. The mixture was shaken at room temperature under a hydrogen atmosphere for 2 hours. The catalyst was then removed by filtration and the filtrate was evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:2) for the elution. There were obtained 2.44 g of 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile of melting point 114°-115° C.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-0c6ef46fa0f54f90ac2f15cba6aa1b50
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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