2-Chloroacetophenone → 2,3-Dimethyl-7-phenacylpyrrolo[2,3-b]pyridine

HRID 1756049Notes

Reaction equation

HRID 1756049 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11].[CH2:12](Cl)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>CC#N>[CH3:1][C:2]1[N:10]=[C:5]2[N:6]([CH2:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:14])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 125323872,3-Dimethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 199167892,3-Dimethyl-7-phenacylpyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,3-dimethylpyrrolo[2,3-b]pyridine (146 mg, 1 mmol) and phenacyl chloride (170 mg, 1.1 mmol) in 3 ml CH3CN was refluxed for 4.5 h. The mixture was allowed to cool and the precipitated product filtered off and washed with a small volume of ice cold CCl4 affording 207 mg (69%) pure title compound as the hydrochloride salt.

Workup

  1. temperatureto cool
  2. filtrationthe precipitated product filtered off
  3. washwashed with a small volume of ice cold CCl4 affording 207 mg (69%) pure title compound as the hydrochloride salt

Sources & evidence

ORD record
ord-94867da8d84b4f77b6b178a7617a42b4
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

Loading…