2-Aminopyridine → HCID 12399252, compound

HRID 1284092Notes

Reaction equation

HRID 1284092 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1)=O.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C(O)C>[N:14]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=2)=[CH:2][N:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=12

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 12399238HCID 12399238, compound

Product 1

HCID 12399252HCID 12399252, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 28 g of 4-(chloroacetyl)phenylacetonitrile, 70 ml of ethanol and 24 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 methanol to give 21 g of 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetonitrile as colorless crystals melting at 175°-177°C with decomposition.

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 methanol

Sources & evidence

ORD record
ord-17b50010f80b4f728d7e4d452e13d517
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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