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

HRID 2203191Notes

Reaction equation

HRID 2203191 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

Conditions

Temperature
80 °C

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° C. 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. customOn completion, it was quenched by 1N NaOH till pH 8
  2. customSolid precipitated
  3. filtrationwas filtered
  4. customvacuum dried

Sources & evidence

ORD record
ord-a02e0f7337cf4f6b9a6a1a99b1700dde
Source dataset
uspto-grants-2016_06
Patent number
US09365570B2

Reaction notes

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