HCID 20093009, compound → HCID 20093029, compound

HRID 274570Notes

Reaction equation

HRID 274570 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)#[N:2].CO[Na]>CO>[C:1]([C:3]1[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)#[N:2]

Participants

4

Reactant 2

HCID 20093009HCID 20093009, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 20093029HCID 20093029, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2'-cyanomethoxy-4-methylbenzophenone (8.9 g) in methanol (750 ml) was added CH3ONa (2.0 g) and molecular sieves (3A, 5 g) and the mixture was heated under reflux for 30 hours. After removal of insoluble materials by filtration, the filtrate was concentrated to dryness. The residue was dissolved in ethyl acetate, followed by removal of insoluble materials by filtration and concentration of the filtrate. The residue was purified by column chromatography on silica gel to afford pale yellow powders (3.34 g, 40%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 hours
  3. customAfter removal of insoluble materials
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated to dryness
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. customfollowed by removal of insoluble materials by filtration and concentration of the filtrate
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-afe75110d39b476aae64b9949d2b6d85
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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