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

HRID 1073936Notes

Reaction equation

HRID 1073936 reaction equation
[CH3:1][C:2]1([CH3:21])[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]([NH2:20])=O)[CH:16]=[CH:17][C:4]=2[O:3]1>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1([CH3:21])[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:20])[CH:16]=[CH:17][C:4]=2[O:3]1

Participants

3

Reactant 1

HCID 198956333,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carboxamide

Product 1

HCID 150389003,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrileYield 98.8%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

7.19 g of (-)-3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carboxamide were heated at 80° C. in 25 ml of phosphorus oxychloride for 30 minutes. The mixture was then cooled and evaporated. The residue was dissolved in dichloromethane and 2M sodium carbonate solution. The organic phase was separated, dried over sodium sulphate and evaporated to give 6.65 g of (-)-3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile which was used without further purification.

Workup

  1. temperatureThe mixture was then cooled
  2. customevaporated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-0c0998ce1acd4261a08e85d0be5f4a11
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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