Hydrochloric Acid → 4-Hydroxy-1-methyl-3-nitropyridin-2(1H)-one
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:14]I.[NH4+].[Cl-].Cl>CN(C=O)C.CC(=O)OCC>[N+:9]([C:3]1[C:4](=[O:8])[N:5]([CH3:14])[CH:6]=[CH:7][C:2]=1[OH:1])([O-:11])=[O:10]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To 4-hydroxy-3-nitro-1H-pyridin-2-one (300 mg, 1.9 mmol) in DMF (5 mL) was added NaH (176 mg, 4.4 mmol, 60% in mineral oil) at 0° C. under N2. After stirring at 0° C. for 30 min, CH3I (272 mg, 1.9 mmol) in DMF (5 mL) was added dropwise, and the mixture was stirred for 2 h at 25° C. Saturated aqueous NH4Cl was added, the pH was adjusted to −3 with 1N HCl and EA extractive work up gave a residue that was triturated with MeOH (0.5 ml):EA (10 mL):PE (5 mL). After filtration, the trituratate was evaporated to give the title compound (300 mg, 91%) as a yellow solid. 1H NMR: (CDCl3, 400 MHz) δ: 7.75 (d, J=7.2 Hz, 1H), 6.17 (d, J=7.2 Hz, 1H) 3.54 (s, 3H). LCMS: 171.0 (M+1)+
Workup
- stirringthe mixture was stirred for 2 h at 25° C
- customup gave a residue that
- customwas triturated with MeOH (0.5 ml)
- filtrationAfter filtration
- customthe trituratate was evaporated
Sources & evidence
- ORD record
- ord-ba0d89d7768e446cbc02ee1b0ccf0863
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034900B2
Reaction notes
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