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

HRID 1934602Notes

Reaction equation

HRID 1934602 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 0.88M). 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 0.88M)
  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-1a45839aebf04c5ab10d039b28addce4
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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