Chloroacetaldehyde → Imidazo[1,2-a]pyridine-8-carbonitrile
Reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl[CH2:11][CH:12]=O>CCO>[N:1]1[CH:11]=[CH:12][N:9]2[CH:8]=[CH:7][CH:6]=[C:3]([C:4]#[N:5])[C:2]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 2-aminonicotinonitrile (1.0 g, 8.39 mmol) in EtOH (10 ml) in a 20 ml sealed vial was added 2-chloroacetaldehyde (1.611 ml, 9.23 mmol) vial was then sealed and heated to 120° C. overnight. Reaction was cooled to RT and quenched with 2N Na2CO3, removed EtOH in vaccuo and extracted with DCMx3. Combined organics and washed with water then brinex2. Dried over sodium sulfate and removed solvent to give title compound as a yellow brown solid (1.2 g, 8.38 mmol, 100% yield) was verified by MS (ES+) C8H5N3 requires: 143 found: 144 [M+H]+
Workup
- customwas then sealed
- customReaction
- temperaturewas cooled to RT
- customquenched with 2N Na2CO3
- customremoved EtOH in vaccuo
- extractionextracted with DCMx3
- washCombined organics and washed with water
- dry with materialDried over sodium sulfate
- customremoved solvent
Sources & evidence
- ORD record
- ord-8c4ee8ddca65462bae95a090d102ba10
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126951B2
Reaction notes
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