Einecs 211-027-4 → HCID 15718534, compound

HRID 1087716Notes

Reaction equation

HRID 1087716 reaction equation
C[O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[C:5]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])=[O:6].[Cl-].[NH+]1C=CC=CC=1>>[OH:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[C:5]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])=[O:6]

Participants

3

Reactant 2

HCID 69401Einecs 211-027-4HCID 157185333-(2-Methoxybenzoyl)benzonitrile

Product 1

HCID 15718534HCID 15718534, compoundYield 60%

Conditions

Temperature
180 °C

Procedure

A mixture of 16 g (0.0675 mol) of 3-(2-methoxybenzoyl)benzonitrile and 50 g (0.43 mol) of pyridinium chloride is heated at 180° C. for 12 hours and the reaction mixture is then cooled to 140° C. and hydrolyzed with an ice/concentrated hydrochloric acid mixture. After stirring for 15 minutes, the expected product is extracted with ethyl acetate. The organic phase obtained is washed with water and then brine (saturated aqueous solution of NaCl) until the pH is neutral, dried over magnesium sulfate and then evaporated under reduced pressure. The resulting oil is purified on silica using a toluene/ethyl acetate mixture as the eluent. After evaporation of the solvents from the eluate, 8.5 g of a yellow solid are obtained (yield: 60%).

Workup

  1. extractionthe expected product is extracted with ethyl acetate
  2. customThe organic phase obtained
  3. washis washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting oil is purified on silica using a toluene/ethyl acetate mixture as the eluent
  7. customAfter evaporation of the solvents from the eluate, 8.5 g of a yellow solid
  8. customare obtained (yield: 60%)

Sources & evidence

ORD record
ord-9fab4b57ed4c46c3b8133905e41285f2
Source dataset
uspto-grants-1990_10
Patent number
US04960758

Reaction notes

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