Ammonium Acetate → 5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile
Reaction equation
[C:1]([O-])(=O)C.[NH4+].C[N:7]([CH3:19])[CH:8]=[CH:9][C:10]1[NH:15][C:14](=[O:16])[C:13]([C:17]#[N:18])=[CH:12][CH:11]=1>CN(C)C=O>[CH3:1][C:19]1[N:7]=[CH:8][CH:9]=[C:10]2[C:11]=1[CH:12]=[C:13]([C:17]#[N:18])[C:14](=[O:16])[NH:15]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
The above preparation was also carried out using ammonium acetate in place of formamidine acetate as follows: A mixture containing 1.305 kg of 1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile, 9 liters of dimethylformamide and 915 g of ammonium acetate was refluxed for five hours. The reaction suspension was cooled to 5° C. for three hours and the precipitated product was collected, washed twice with cold 60/40 by volume of dimethylformamide/water, twice with cold ethanol, once with ether and dried to yield 826 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile, m.p. 275°-277° C.
Workup
- customThe above preparation
- temperaturewas refluxed for five hours
- customthe precipitated product was collected
- washwashed twice with cold 60/40 by volume of dimethylformamide/water, twice with cold ethanol, once with ether
- customdried
Sources & evidence
- ORD record
- ord-4269c3c9dbc64085af60cb8211b17651
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04559347
Reaction notes
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