HCID 22405140, compound → 168045-49-6
Reaction equation
C([O:3][C:4]([CH2:6][N:7]([C:17](=[O:27])[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O)=O)C>C(O)C.C(O)(=O)C.[Fe]>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([N:7]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:14][C:4](=[O:3])[CH2:6]2)=[O:27])=[CH:19][CH:20]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of N-ethoxycarbonylmethyl-N-(4-nitrobenzoyl)-2-nitroaniline (500 mg) and iron powder (374 mg) in a mixture of ethanol (10 ml) and acetic acid (1 ml) was heated at 80° C. for 3 hours and the solution was cooled to ambient temperature. The mixture was filtered through celite and the filtrate was evaporated in vacuo. The residue was dissolved in chloroform (20 ml) and the solution was neutralized with aqueous sodium hydrogen carbonate. The solution was filtered through celite and the organic filtrate was washed with brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give a crude oil. The oil was purified by silica gel column (10 g, 2% methanol in chloroform) to give 4-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoxalin-2-one (58 mg) as a pale yellow powder.
Workup
- temperaturethe solution was cooled to ambient temperature
- filtrationThe mixture was filtered through celite
- customthe filtrate was evaporated in vacuo
- dissolutionThe residue was dissolved in chloroform (20 ml)
- filtrationThe solution was filtered through celite
- washthe organic filtrate was washed with brine
- dry with materialThe solution was dried over magnesium sulfate
- customthe solvent was evaporated in vacuo
- customto give a crude oil
- customThe oil was purified by silica gel column (10 g, 2% methanol in chloroform)
Sources & evidence
- ORD record
- ord-d0beeaae02404aa3ae474cbcc801bf1b
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521170
Reaction notes
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