4-Methoxybenzonitrile → HCID 22503129, compound

HRID 1006917Notes

Reaction equation

HRID 1006917 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:4]=1[C:5]([O:7]CC)=O.C([N-]C(C)C)(C)C.[Li+].C1CCCCC1.[C:29](#[N:38])[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:4]=1[C:5](=[O:7])[NH:38][C:29]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)=[CH:14]2

Participants

5

Reactant 3

HCID 701294-MethoxybenzonitrileHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl esterHCID 86604122LDA cyclohexane

Product 1

HCID 22503129HCID 22503129, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 2-methoxy-6-methylbenzoate (5.011 g) was dissolved in tetrahydrofuran (20 ml), followed by the addition of 1.5M lithium diisopropylamide/cyclohexane solution (19 ml) in nitrogen atmosphere at −70° C. The resulting mixture was stirred for 45 min. Anisonitrile (3.462 g)/tetrahydrofuran (10 ml) solution was added to the reaction mixture. The cooling bath was removed, and then the mixture was stirred for 100 min. An aqueous solution of saturated ammonium chloride and ethyl acetate were added to the reaction solution, and the mixture was stirred for 30 min. The resulting insoluble matters were collected by filtration, and then washed with ethyl acetate and water, to give the title compound as a pale yellow solid (991 mg, yield; 13%).

Workup

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred for 100 min
  3. additionAn aqueous solution of saturated ammonium chloride and ethyl acetate were added to the reaction solution
  4. stirringthe mixture was stirred for 30 min
  5. filtrationThe resulting insoluble matters were collected by filtration
  6. washwashed with ethyl acetate and water

Sources & evidence

ORD record
ord-262e55af71d049008721b89504d161f8
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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