N-methyl-2-pyrrolidone → HCID 13938643, compound

HRID 2309405Notes

Reaction equation

HRID 2309405 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([CH3:19])[CH:12]=1)=[C:5]2[CH3:20].[Cu](C#N)[C:22]#[N:23].CN1CCCC1=O>C(OCC)(=O)C>[C:22]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([CH3:19])[CH:12]=1)=[C:5]2[CH3:20])#[N:23]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 13938623HCID 13938623, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 13938643HCID 13938643, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.32 g of 5-bromo-2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole and 0.54 g of copper cyanide were added to 10 ml of N-methylpyrrolidone, and the mixture was refluxed for 4 hours. To the reaction mixture was added ethyl acetate, and the mixture was washed with 20% aqueous ammonia solution and water, and dried. The solvent was evaporated, and the residue was purified by silica gel column chromatography. Recrystallization of the crude product from ether-petroleum ether gave 5-cyano-2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. washthe mixture was washed with 20% aqueous ammonia solution and water
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography
  6. customRecrystallization of the crude product from ether-petroleum ether

Sources & evidence

ORD record
ord-f6bfe45456924699b95646c508b481bb
Source dataset
uspto-grants-1987_09
Patent number
US04695581

Reaction notes

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