Piperidine → 2-aminoquinoline-3-carbonitrile
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C(#N)[CH:11]([CH2:13][C:14]#[N:15])O.[NH:17]1CCCCC1>C(O)C>[NH2:15][C:14]1[C:13]([C:11]#[N:17])=[CH:4][C:3]2[C:2](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-aminobenzaldehyde (2.42 g; 20 mmol) in dry ethanol (60 mL) was added malonitrile (1.89 mL; 30 mmol) and piperidine (0.988 mL; 10 mmol). The reaction mixture was partitioned in four sealed tubes and heated at 100° C. for 24 h. The volatiles were removed under reduced pressure and the remaining crude was purified by flash-chromatography using a gradient of ethyl acetate (5-80%) in dichloromethane as eluent to furnish 1.94 g (57%) of 2-aminoquinoline-3-carbonitrile as an ochre solid. ESI/APCI: 170 (M+H).
Workup
- customThe reaction mixture was partitioned in four sealed tubes
- customThe volatiles were removed under reduced pressure
- customthe remaining crude was purified by flash-chromatography
Sources & evidence
- ORD record
- ord-98f3bdf7829a43f99b639a38cbfd36a9
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09132129B2
Reaction notes
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