HCID 14857333, compound → HCID 9926186, compound

HRID 1195809Notes

Reaction equation

HRID 1195809 reaction equation
[CH3:1][C:2]1([CH3:28])[CH:11]([OH:12])[CH:10]([C:13]2[C:14](=[O:25])[N:15](COCCOC)[CH:16]=[CH:17][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:26]#[N:27])[CH:8]=2)[O:3]1>[Zn+2].[Br-].[Br-].ClCCl>[CH3:1][C:2]1([CH3:28])[CH:11]([OH:12])[CH:10]([C:13]2[C:14](=[O:25])[NH:15][CH:16]=[CH:17][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:26]#[N:27])[CH:8]=2)[O:3]1

Participants

4

Reactant 1

HCID 14857333HCID 14857333, compound

Product 1

HCID 9926186HCID 9926186, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 384 mg of 2,2-dimethyl-4-[1-(2-methoxyethoxymethyl)-1,2-dihydro-2-oxo-3-pyridyl]-6-cyano-3-chromanol [obtainable from 1-(2-methoxyethoxy-methyl)-1,2-dihydro-2-oxopyridine and 2,2-dimethyl-3,4-epoxy-6-cyanochroman], 600 mg of finely powdered ZnBr2 and 4 ml of dichloromethane is stirred at 25° for 16 hours. The mixture is washed with saturated NaHCO3 solution, then with saturated NaCl solution, the wash solutions are extracted with ether, and the organic phases are combined and further worked up in the customary manner. 2,2-Dimethyl-4-(1,2-dihydro-2-oxo-3-pyridyl)-6-cyano-3-chromanol is obtained; m.p. 246°-247°.

Workup

  1. washThe mixture is washed with saturated NaHCO3 solution
  2. extractionwith saturated NaCl solution, the wash solutions are extracted with ether

Sources & evidence

ORD record
ord-85586e85b5924502882202c75963f608
Source dataset
uspto-grants-1992_05
Patent number
US05112839

Reaction notes

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