2-Amino-4-methylpyridine → 2-(Chloromethyl)-7-methylimidazo[1,2-a]pyridine

HRID 728182Notes

Reaction equation

HRID 728182 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[NH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1>C(#N)C>[Cl:1][CH2:2][C:3]1[N:7]=[C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]2[CH:5]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 107931,3-Dichloroacetone

Product 1

HCID 140427782-(Chloromethyl)-7-methylimidazo[1,2-a]pyridineYield 23.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,3-dichloroacetone (30.0 g) and 2-amino-4-picoline (63.9 g) in acetonitrile (210 ml) was refluxed for 1 hour. Evaporation of a solvent gave a residue, which was purified by a column chromatography on silica gel eluting with a mixture of dichloromethane and ethyl acetate (1:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-chloromethyl-7-methylimidazo[1,2-a]pyridine (10.21 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customEvaporation of a solvent
  3. customgave a residue, which
  4. customwas purified by a column chromatography on silica gel eluting with a mixture of dichloromethane and ethyl acetate (1:1, V/V)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f2971b76cd674f80a384dc5111eb280b
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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