Indole → 6-cyano-4-methyl-1H-indole-3-carboxylic acid

HRID 57317Notes

Reaction equation

HRID 57317 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[CH:3]=C1.C([Cu])#N.C[N:14]1[C:18](=O)[CH2:17][CH2:16][CH2:15]1.C[C:21](=[O:25])[O:22]CC>>[C:9]([C:4]1[CH:3]=[C:18]2[C:17]([C:16]([C:21]([OH:25])=[O:22])=[CH:15][NH:14]2)=[C:6]([CH3:7])[CH:5]=1)#[N:1]

Participants

5

Reactant 4

HCID 798IndoleHCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 178418546HCID 178418546, compound

Product 1

HCID 1186446086-cyano-4-methyl-1H-indole-3-carboxylic acidYield 45.6%

Conditions

Temperature
180 °C

Procedure

A mixture of compound 1 (10.0 g, 50.0 mmol), CuCN (9.0 g, 100 mmol) and NMP (60 mL) was heated at 180° C. for 6 h. The mixture was cooled to room temperature, diluted with EA, then washed with H2O, brine, dried and concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc=10/1) to give the desired product (3.30 g, 22.8 mmol, 45.6%) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with H2O, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (petroleum ether/EtOAc=10/1)

Sources & evidence

ORD record
ord-d72ba7057db346ae94ec474ab89a0291
Source dataset
uspto-grants-2016_09
Patent number
US09434724B2

Reaction notes

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