Dabco → 1-Methyl-1H-indole-3-carbonitrile

HRID 488536Notes

Reaction equation

HRID 488536 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].[CH2:12]1N2CCN(CC2)C1>CCOC(C)=O.O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 9237DabcoHCID 2302823-Cyanoindole

Product 1

HCID 23076811-Methyl-1H-indole-3-carbonitrileYield 987.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-cyanoindole (1.0 g, 7.03 mmol) in DMC (10 mL), DABCO (0.079 g, 0.70 mmol) is added and the resulting solution is heated to reflux for 8 h. The reaction is cooled to RT, and diluted with EtOAc (40 mL) and H2O (40 mL). The organic layer is separated and washed in sequence with H2O (50 mL), 10% aqueous citric acid (2×40 mL) and H2O (4×40 mL). The organic layer is dried over anhydrous Na2SO4, filtered and concentrated under vacuum to give 3-cyano-1-methylindole (about 1.08 g, 98%) as an oil: 1H NMR (CDCl3) δ7.74 (d, 1H), 7.53 (s, 1H), 7.40-7.28 (m, 3H), 3.83 (s, 3H); 13C NMR (CDCl3) 136.0, 135.6, 127.8, 123.8, 122.1, 119.8, 116.0, 110.4, 85.4, 33.6; MS m/z 156 [M+1]+.

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureto reflux for 8 h
  3. customThe organic layer is separated
  4. washwashed in sequence with H2O (50 mL), 10% aqueous citric acid (2×40 mL) and H2O (4×40 mL)
  5. dry with materialThe organic layer is dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5dfce167463249f49440ce33cd2da5bb
Source dataset
uspto-grants-2005_12
Patent number
US06972336B2

Reaction notes

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