Sodium → HCID 17966448, compound

HRID 227589Notes

Reaction equation

HRID 227589 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[C:7]([N+]([O-])=O)[CH:6]=[CH:5][N:4]=1)#[N:2].[CH3:14][O-:15].[Na+].[Na]>CO.O>[C:1]([C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:15][CH3:14])[CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22310829HCID 22310829, compound

Product 1

HCID 17966448HCID 17966448, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

3 g (0.017 moles) of 2-cyano-3-methoxy-4-nitropyridine obtained in Example a) and a sodium methoxide solution prepared from 0.77 g (0.033 moles) of sodium and 65 ml of methanol are stirred at ambient temperature for 4 hours. There is added 100 ml of water, the methanol is eliminated and the aqueous phase is extracted with dichloromethane. The organic phase is washed with water, dried, concentrated and the residue chromatographed (ethyl acetate/heptane, 1:1) to obtain 1.96 g (72% yield) of a white solid (MP=133° C.).

Workup

  1. extractionthe aqueous phase is extracted with dichloromethane
  2. washThe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated
  5. customthe residue chromatographed (ethyl acetate/heptane, 1:1)

Sources & evidence

ORD record
ord-89135b4888174b1aa29260401b0a144e
Source dataset
uspto-grants-2009_07
Patent number
US07560565B2

Reaction notes

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