2-Aminopyridine → HCID 12399255, compound

HRID 1284093Notes

Reaction equation

HRID 1284093 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([NH2:14])=[O:13])=[CH:7][CH:6]=1)=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C(O)C>[N:16]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([NH2:14])=[O:13])=[CH:7][CH:6]=2)=[CH:2][N:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=12

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 12399241HCID 12399241, compound

Product 1

HCID 12399255HCID 12399255, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9 g of 2-[4-(chloroacetyl)phenyl]propionamide, 30 ml of ethanol and 7.6 g of 2-aminopyridine is heated under reflux for 2 hours. The ethanol is distilled off under reduced pressure, and water is added to the residue. The crystalline precipitate is filtered off and recrystallized from aqueous dimethylformamide to give 6.9 g of 2-[4-(imidazo[1,2-a]pyridin-2-yl)phenyl]propionamide as colorless scales melting at 219°-220°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. distillationThe ethanol is distilled off under reduced pressure, and water
  4. additionis added to the residue
  5. filtrationThe crystalline precipitate is filtered off
  6. customrecrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-d35c45042bea4432b7058b112ce755e5
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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