Chloroform → HCID 90404301, compound

HRID 1505661Notes

Reaction equation

HRID 1505661 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([NH2:14])=O)[NH:9]2)=[CH:5][C:4]=1[CH3:15].P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)Cl>O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]#[N:14])[NH:9]2)=[CH:5][C:4]=1[CH3:15]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 90404094HCID 90404094, compound

Product 1

HCID 90404301HCID 90404301, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 202 mg of 6-methoxy-5-methyl-1H-indole-2-carboxamide (1 mmol), 0.47 mL of phosphorus oxychloride (5 mmol) and 3 mL of chloroform was refluxed for 2 hs. Then cooled solution was poured into 10 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 116 mg of 6-methoxy-5-methyl-1H-indole-2-carbonitrile. 1H NMR (600 MHz, CDCl3): δ 8.26 (br, 1H), 7.37 (s, 1H), 7.06 (s, 1H), 6.76 (s, 1H), 3.88 (s, 1H), 2.28 (s, 3H).

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-8c08a2b1b6d14a309cc2473bc1408e96
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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