Ethanol → 2-(cyclopropylamino)nicotinonitrile
Reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(O)C.[CH:13]1([NH2:16])[CH2:15][CH2:14]1>O>[CH:13]1([NH:16][C:2]2[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:15][CH2:14]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A reaction flask equipped with a mechanical stirrer, temperature controller, condenser and addition funnel was charged with 2-chloro-3-pyridinecarbonitrile (69.25 g, 0.50 mol), 300 ml of ethanol and 200 ml of water. With agitation, cyclopropylamine ( 114g, 2.0 mol) was added dropwise over 30 minutes at a temperature<30° C. When the addition was completed, the stirred reaction mixture was heated to reflux temperature for 20 hours. The reaction mixture was cooled to 60° C. and then 350 ml of excess cyclopropylamine and ethanol were removed by vacuum distillation using water aspirator vacuum. The remaining aqueous solution was cooled to ambient temperature and allowed to stand overnight. The solid product was collected by filtration and the filter cake rinsed with water. The yield was 81.51 g (theoretical yield is 79.5 g).
Workup
- customA reaction flask equipped with a mechanical stirrer
- additiontemperature controller, condenser and addition funnel
- additionWhen the addition
- customthe stirred reaction mixture
- temperaturewas heated
- temperatureto reflux temperature for 20 hours
- custom350 ml of excess cyclopropylamine and ethanol were removed by vacuum distillation
- temperatureThe remaining aqueous solution was cooled to ambient temperature
- filtrationThe solid product was collected by filtration
- washthe filter cake rinsed with water
Sources & evidence
- ORD record
- ord-0d2a6c38c7744a3ab3442909bf9e2200
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680383B1
Reaction notes
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