Propionic Acid → 2-ethyl-1-phenyl-1H-imidazo[4,5-c]pyridine

HRID 2177625

Reaction equation

HRID 2177625 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](O)(=O)[CH2:16][CH3:17]>P(Cl)(Cl)(Cl)=O>[CH2:16]([C:17]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]=1)[CH3:15]

Participants

4

Reactant 2

HCID 1032Propionic AcidHCID 105836754-N-phenylpyridine-3,4-diamine

Product 1

HCID 904095952-ethyl-1-phenyl-1H-imidazo[4,5-c]pyridineYield 19.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of N4-phenylpyridine-3,4-diamine (8.0 g, 37.2 mmol), propionic acid (2.7 g, 37.2 mmol) and phosphorous oxychloride (50 mL) was stirred at reflux for 10 h. The reaction was purified by silica gel chromatography using ethyl acetate to afford the product as a solid (1.6 g, 19%).

Workup

  1. temperatureat reflux for 10 h
  2. customThe reaction was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7cd3cb1fb65b4173a4000af600bf5e42
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Linked notes

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