Chloroacetaldehyde → Methyl imidazo(1,2-a)pyridine-6-carboxylate

HRID 383315Notes

Reaction equation

HRID 383315 reaction equation
Cl[CH2:2][CH:3]=O.[CH3:5][O:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[N:10][CH:9]=1>C(O)C>[CH3:5][O:6][C:7]([C:8]1[CH:13]=[CH:12][C:11]2[N:10]([CH:2]=[CH:3][N:14]=2)[CH:9]=1)=[O:15]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 737487Methyl 6-aminonicotinate

Product 1

HCID 2764326Methyl imidazo(1,2-a)pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 50% aq. chloroacetaldehyde (1.1 eq, 36 mmol, 4.6 ml) in ethanol (120 ml) is added 6-amino-nicotinic acid methyl ester (1 eq, 33 mmol, 5 g) at room temperature. The reaction mixture is heated at reflux for 18 hours. The solvent is removed in vacuo and the crude product is dissolved in water (400 ml). The aqueous solution is treated with sodium bicarbonate to pH=8 and extracted with DCM (3×250 ml). The organic layer is dried (MgSO4) and evaporated to give the title compound as a beige solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent is removed in vacuo
  4. dissolutionthe crude product is dissolved in water (400 ml)
  5. additionThe aqueous solution is treated with sodium bicarbonate to pH=8
  6. extractionextracted with DCM (3×250 ml)
  7. dry with materialThe organic layer is dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-698543befdbd4076a94a7c188b555497
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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