Acetic Acid → N-(6-methoxy-5-methyl-2-nitro-3-pyridinyl)acetamide
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[CH3:10].[N+:11]([O-:14])(O)=[O:12].[OH-].[Na+].[C:17](O)(=[O:19])[CH3:18]>>[CH3:1][O:2][C:3]1[N:8]=[C:7]([N+:11]([O-:14])=[O:12])[C:6]([NH:9][C:17](=[O:19])[CH3:18])=[CH:5][C:4]=1[CH3:10]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Anhydrous acetic acid (20 ml) was added to 6-methoxy-5-methyl-3-pyridineamine (1.18 g, 8.54 mmol) under ice cooling, and stirred at 0° C. for 20 minutes and at room temperature further for 1 hour. The reaction mixture was cooled at 0° C. again, fuming nitric acid (2 ml) was dropped thereto, and the mixture was stirred at 0° C. for 1 hour and 55 minutes and at room temperature further for 1 hour and 45 minutes. The reaction mixture was poured onto ice and adjusted to pH 9 with a 5N sodium hydroxide solution, extracted with ethyl acetate, and then the solvent was evaporated, thereby yielding the title compound (1.94 g) as a yellow solid crude product.
Workup
- temperatureThe reaction mixture was cooled at 0° C. again
- stirringthe mixture was stirred at 0° C. for 1 hour and 55 minutes and at room temperature further for 1 hour and 45 minutes
- additionThe reaction mixture was poured onto ice
- extractionextracted with ethyl acetate
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-10b9455954c449efbe7dfe5395c89169
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781452B2
Reaction notes
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