Chloroacetaldehyde → 7-Methylimidazo[1,2-a]pyridine-8-carbonitrile

HRID 2167679Notes

Reaction equation

HRID 2167679 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].Cl[CH2:12][CH:13]=O>O>[CH3:10][C:6]1[CH:7]=[CH:8][N:9]2[CH:12]=[CH:13][N:1]=[C:2]2[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 103968872-Amino-4-methylpyridine-3-carbonitrile

Product 1

HCID 768497047-Methylimidazo[1,2-a]pyridine-8-carbonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of compound 2-amino-4-methylnicotinonitrile (1 equiv.) in water was added chloroacetaldehyde (55% aq. solution) (1.2 equiv.) and the reaction was heated at 80 oC for 16 h. On completion, it was quenched by 1N NaOH till pH 8. Solid precipitated was filtered and vacuum dried to afford the title compound (75% yield).

Workup

  1. temperaturethe reaction was heated at 80 oC for 16 h
  2. customOn completion, it was quenched by 1N NaOH till pH 8
  3. customSolid precipitated
  4. filtrationwas filtered
  5. customvacuum dried

Sources & evidence

ORD record
ord-1bd35f134caf407ea9519a2d6b665761
Source dataset
uspto-grants-2015_06
Patent number
US09045477B2

Reaction notes

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