4-[1,1-Dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrile → 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile

HRID 1073881Notes

Reaction equation

HRID 1073881 reaction equation
[CH3:1][C:2]([CH3:20])([O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1([CH3:20])[CH:3]=[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)[C:19]2[CH:18]=[C:15]([C:16]#[N:17])[CH:14]=[CH:13][C:12]=2[O:11]1

Participants

3

Reactant 1

HCID 157329624-[1,1-Dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

12 98 g of 4-[1,1-dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrile were dissolved in 50 ml of 1,2-dichlorobenzene and heated at reflux for 5 hours. After cooling the mixture was evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:2), ethyl acetate/petroleum ether (1:1) and ethyl acetate for the elution. There were obtained 6.5 g of 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile of melting point 106-108° C. after recrystallization from cyclohexane.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling the mixture
  4. customwas evaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-fd701919de48472da0e8ed4309919fe4
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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