Potassium Carbonate → 1-Methyl-1H-indole-3-carbonitrile

HRID 2268154Notes

Reaction equation

HRID 2268154 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1.[C:12](=O)([O-])[O-].[K+].[K+].C(=O)(OC)OC>>[CH3:12][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 12021Dimethyl CarbonateHCID 2302823-Cyanoindole

Product 1

HCID 23076811-Methyl-1H-indole-3-carbonitrileYield 189.4%

Conditions

Temperature
130 °C

Procedure

A mixture of indole-3-carbonitrile (1.0 g, 7.03 mmole), potassium carbonate (0.5 g), N,N-dimethytformamide (10 mL) and dimethyl carbonate (1.8 mL, 21.4 mmol) was stirred and heated to reflux (˜130° C.). The reaction (monitored by HPLC) was complete within 3.5 h. The reaction mixture was then cooled to 3° C. and ice cold water (25 mL) was added slowly. The resulting oily suspension was extracted with tert-butyl methyl ether (40 mL) and the organic phase was washed with water (3×25 mL), dried and evaporated in vacuo to obtain 1.07 g of the product, 1-methylindole-3-carbonitrile, as a dark oil (97.4% yield).

Workup

  1. temperatureheated
  2. customThe reaction (monitored by HPLC)
  3. temperatureThe reaction mixture was then cooled to 3° C.
  4. extractionThe resulting oily suspension was extracted with tert-butyl methyl ether (40 mL)
  5. washthe organic phase was washed with water (3×25 mL)
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4253ba63d47c4014850007f5b131a3c0
Source dataset
uspto-grants-2001_12
Patent number
US06326501B1

Reaction notes

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