Hydrochloric Acid → 4-Hydroxy-1-methyl-3-nitro-1,2-dihydroquinolin-2-one
Reaction equation
C(O[C:4](=[O:9])[CH2:5][N+:6]([O-:8])=[O:7])C.[H-].[Na+].[H][H].[CH3:14][N:15]1C(=O)O[C:18](=[O:19])[C:17]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:16]12.Cl>CC(N(C)C)=O>[OH:19][C:18]1[C:17]2[C:16](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]([CH3:14])[C:4](=[O:9])[C:5]=1[N+:6]([O-:8])=[O:7]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A solution of ethyinitroacetate (15.96 g, 120 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 5.28 g, 132 mmol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and cooled to room temperature. A solution of N-methylisatoic anhydride (23.38 g, 132 mmol) in dimethylacetamide was added slowly and heated overnight at 120° C. The mixture was cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 7.1 g (27%) of yellow solids. Mp 193° C. 1H NMR (DMSO-d6): δ 3.60 (s, 3H), 7.37 (t, J=7.6 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.77 (t, J=7.5 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H). EIMS m/z 221 (M+1), 243 (M+23). Anal. (C10H8N2O4) C, H, N.
Workup
- temperaturecooled to room temperature
- temperatureheated overnight at 120° C
- temperatureThe mixture was cooled to room temperature
- customThe solids formed
- filtrationwere filtered
- washwashed several times by water
Sources & evidence
- ORD record
- ord-a3dbf0506ad7475ca9570176c601acff
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07192961B2
Reaction notes
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