Chloroacetaldehyde → 5-Methylimidazo[1,2-a]pyridine-6-carbonitrile hydrochloride

HRID 552817Notes

Reaction equation

HRID 552817 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[N:3]=1.[Cl:11][CH2:12][CH:13]=O>C(O)C>[ClH:11].[CH3:10][C:4]1[N:3]2[CH:12]=[CH:13][N:1]=[C:2]2[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 27946626-Amino-2-methylpyridine-3-carbonitrile

Product 1

HCID 671637165-Methylimidazo[1,2-a]pyridine-6-carbonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-amino-2-methylnicotinonitrile (960 mg) in ethanol (34 ml) was added a 40% aqueous chloroacetaldehyde solution (2.36 ml) at 60° C. The reaction mixture was refluxed for 8 hours. The resulting precipitates were collected by filtration to obtain 5-methylimidazo[1,2-a]pyridine-6-carbonitrile hydrochloride (580 mg) as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1dbbd8def99042788ccdb14a16def3dd
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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