Chloroform → HCID 90405189, compound

HRID 1505658Notes

Reaction equation

HRID 1505658 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:13]([NH2:15])=O)[NH:7]2.P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)Cl>O>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:13]#[N:15])[NH:7]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 90405643HCID 90405643, compound

Product 1

HCID 90405189HCID 90405189, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 79 mg of 4-methoxy-5-methyl-1H-indole-2-carboxamide (0.39 mmol), 0.19 mL of phosphorus oxychloride (2 mmol) and 1.5 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 51 mg of 4-methoxy-5-methyl-1H-indole-2-carbonitrile.

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-737521f778834f9fa40a31bbfdfb8b35
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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