2-Amino-3-methylpyridine → 2-n-Propyl-3-ethoxycarbonyl-8-methylimidazo[1,2-a]pyridine

HRID 326674Notes

Reaction equation

HRID 326674 reaction equation
Cl[CH:2]([C:9](=O)[CH2:10][CH2:11]C)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1>C(O)CO.COC>[CH2:9]([C:2]1[N:14]=[C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]2[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 19735617Ethyl 2-chloro-3-oxo-hexane carboxylate

Product 1

HCID 197356202-n-Propyl-3-ethoxycarbonyl-8-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 21863332Dimethyl ether ethylene glycolSolvent

Procedure

2.3 g (11.9 mMol) of ethyl 2-chloro-3-oxo-hexane carboxylate and 2.6 g (23.8 mMol) of 2-amino-3-picoline are dissolved in 10 ml of ethyleneglycol-dimethylether and refluxed for 3 days. Then the solvent is evaporated off in vacuo and the residue is taken up in water/ethyl acetate 1:1. After the extraction the organic phase is separated off, washed with saturated saline solution, dried over magnesium sulphate and evaporated down. The residue is purified over a silica gel column (particle size: 0.063 to 0.02 mm), using as eluant mixtures of petroleum ether/ethyl acetate of increasing polarity (85:15, 80:20 and 1:1). The uniform fractions are evaporated down in vacuo.

Workup

  1. temperaturerefluxed for 3 days
  2. customThen the solvent is evaporated off in vacuo
  3. extractionAfter the extraction the organic phase
  4. customis separated off
  5. washwashed with saturated saline solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated down
  8. customThe residue is purified over a silica gel column (particle size: 0.063 to 0.02 mm)
  9. temperatureof increasing polarity (85:15, 80:20 and 1:1)
  10. customThe uniform fractions are evaporated down in vacuo

Sources & evidence

ORD record
ord-a4daee22331c43249f48979b9c25e5de
Source dataset
uspto-grants-1993_12
Patent number
US05270322

Reaction notes

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