N-methyl-2-pyrrolidone → 1-Methyl-1H-indole-6-carbonitrile

HRID 381312Notes

Reaction equation

HRID 381312 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH3:12][N:13]1CCCC1=O>>[C:12]([C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1)#[N:13]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 155468546-Bromo-1-methyl-1H-indole

Product 1

HCID 153844931-Methyl-1H-indole-6-carbonitrile

Conditions

Temperature
150 °C

Procedure

Cuprous cyanide (12.8 g, 143 mmol) was added to a stirred solution of 6-bromo-1-methylindole (10 g, 47 mmol) in N-methylpyrrolidinone (60 ml) under a nitrogen atmosphere. The reaction mixture was heated at 150° C. for 48 h. The reaction mixture was cooled and partitioned between ethyl acetate (200 ml) and aqueous ammonia (200 ml of 0.88 M). The organic layer was washed with brine (3×200 ml), dried (MgSO4) and concentrated. Flash column chromatography (elution with 70% hexane/30% ethyl acetate) gave the product as a crystalline white solid (5.3 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate (200 ml) and aqueous ammonia (200 ml of 0.88 M)
  3. washThe organic layer was washed with brine (3×200 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washFlash column chromatography (elution with 70% hexane/30% ethyl acetate)

Sources & evidence

ORD record
ord-b31708622c534fc6a7d03de21d0b2ed2
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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