1-[(Diethoxyphosphoryl)methyl]-8-nitro-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one → 8-Amino-1[(diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one
Reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[N:14]2[C:15]3[C:20]([NH:21][C:22](=[O:23])[C:13]2=[N:12][N:11]=1)=[CH:19][C:18]([C:24]([F:27])([F:26])[F:25])=[C:17]([N+:28]([O-])=O)[CH:16]=3)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>C(O)C.[Ni]>[NH2:28][C:17]1[CH:16]=[C:15]2[C:20]([NH:21][C:22](=[O:23])[C:13]3[N:14]2[C:10]([CH2:9][P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])=[N:11][N:12]=3)=[CH:19][C:18]=1[C:24]([F:25])([F:26])[F:27]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1-[(diethoxyphosphoryl)methyl]-8-nitro-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one (3.25 g, 7.2 mmol) in 500 ml of ethanol was hydrogenated at 40 psi and room temperature for 6 h in the presence of Raney-Ni. The catalyst and precipitated solid was isolated by filtration and washed with ethanol. The ethanolic filtrate was discharged, and the filter-cake was washed with N,N-dimethylformamide. The filtrate was evaporated, and the residue was triturated with water to give the title compound as a light yellow solid (2.4 g, 80%), m.p. 260°-263° C.; 1H-NMR (DMSO-d6): δ 1.18 (t, 6H), 4.07 (quint, 4H), 4.13 (d, 2H), 5.74 (br s, 2H), 7.42 (s, 1H), 7.69 (s, 1H), 11.8 (s, 1H).
Workup
- customThe catalyst and precipitated solid
- customwas isolated by filtration
- washwashed with ethanol
- washthe filter-cake was washed with N,N-dimethylformamide
- customThe filtrate was evaporated
- customthe residue was triturated with water
Sources & evidence
- ORD record
- ord-3a2e70f603ab464d93b1933d97ce6fde
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05559106
Reaction notes
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