Chloroform → 5-methyl-1H-indole-2-carbonitrile

HRID 1505653

Reaction equation

HRID 1505653 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=O)=[CH:5]2.P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)Cl>O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]#[N:13])=[CH:5]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 47776705-methyl-1H-indole-2-carboxamide

Product 1

HCID 199947895-methyl-1H-indole-2-carbonitrileYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 340 mg of 5-methylindole-2-carboxamide (1.95 mmol), 1.5 g of phosphorus oxychloride (9.75) and 8 mL of chloroform was refluxed for 2 hs. Then cooled solution was poured into 20 mL of water and stirred for 1 hr. After separation the organic layer was dried over sodium sulfate and concentrated. The residue was purified on silica gel column using hexane-ethyl acetate 5:1 to afford 245 mg of 5-methyl-1H-indole-2-carbonitrile. 1H NMR (600 MHz, CDCl3): δ 8.61 (br, 1H), 7.44 (s, 1H), 7.30 (d, 1H, J=8.4 Hz), 7.21 (d, 1H, J=8.4 Hz), 7.11 (s, 1H), 2.44 (s, 3H). 13C NMR (150 MHz, CDCl3): δC 135.34, 131.25, 128.28, 126.53, 121.33, 114.41, 113.95, 111.39, 106.11, 21.36.

Workup

  1. temperaturewas refluxed for 2 hs
  2. customAfter separation the organic layer
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-445cc558961349e6828db1c8718c75d4
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Linked notes

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