Acetic Acid → 5-methyl-5,6,7,8-tetrahydro-1,6-naphthyridine
Reaction equation
[N+:1]([CH3:4])([O-])=O.[NH:5]1[CH2:10][CH2:9]CCC1.C(O)(=O)C.[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:9][CH:10]1[NH:5][CH2:16][CH2:17][C:18]2[N:1]=[CH:4][CH:15]=[CH:20][C:19]1=2Participants
5
Procedure
To a solution of aldehyde A (1 mol) in benzene (approx. 20 ml per 1 g of the starting compound) nitromethane (1.2 mol), piperidine (0.1 mol) and acetic acid (0.1 mol) are added. The reaction mixture is refluxed for 2.5 h with azeotrope removing of water. Then, the solvent is evaporated in vacuo. The residue is triturated with cold methanol, filtered, washed with cold methanol that resulted in product crystals in good to moderate yields.
Workup
- temperatureThe reaction mixture is refluxed for 2.5 h with azeotrope
- customremoving of water
- customThen, the solvent is evaporated in vacuo
- customThe residue is triturated with cold methanol
- filtrationfiltered
- washwashed with cold methanol that
- customresulted in product crystals in good to moderate yields
Sources & evidence
- ORD record
- ord-f8d440ea64f7407faab9167f63e427fb
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985753B2
Reaction notes
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