Chloroacetaldehyde → Imidazo[1,2-a]pyridine-8-carboxylic acid

HRID 1423030Notes

Reaction equation

HRID 1423030 reaction equation
Cl[CH2:2][CH:3]=O.[NH2:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]>C(O)C>[N:5]1[CH:2]=[CH:3][N:14]2[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]=12

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 729302-Aminonicotinic acid

Product 1

HCID 11715357Imidazo[1,2-a]pyridine-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Chloroacetaldehyde (45% aqueous solution) (6.6 mL, 38 mmol) is added to the stirred solution of 2-aminonicotinic acid (5.0 g, 25 mmol) in ethanol (35 mL) and warmed at reflux for 14 hours. The reaction mixture is concentrated and the crude material is triturated with EtOH-Et2O to afford imidazo[1,2-a]pyridine-8-carboxylic acid. Mp: 296-299° C.

Workup

  1. temperaturewarmed
  2. temperatureat reflux for 14 hours
  3. concentrationThe reaction mixture is concentrated
  4. customthe crude material is triturated with EtOH-Et2O

Sources & evidence

ORD record
ord-765518d27083414d94bc6a3d51089fa6
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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