Nitric Acid → 3-Bromo-2-methyl-7-nitrothieno[3,2-c]pyridin-4(5h)-one
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:10]2[C:11](=[O:15])[NH:12][CH:13]=[CH:14][C:9]=2[S:8][C:7]=1[CH3:16]>S(=O)(=O)(O)O>[Br:5][C:6]1[C:10]2[C:11](=[O:15])[NH:12][CH:13]=[C:14]([N+:1]([O-:4])=[O:2])[C:9]=2[S:8][C:7]=1[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of nitric acid (1.68 mL, 70%, 26.8 mmol) in sulfuric acid (5 mL) was added dropwise to a 0° C. solution of Example 66A (3.27 g, 13.4 mmol) in sulfuric acid (15 mL). The resulting mixture was stirred at 0° C. for 1 hour, warmed to room temperature overnight, and poured into ice water. The resulting precipitate was collected by filtration, washed with water, and dried in a vacuum oven to provide 2.47 g (64% yield) of the desired product. MS (ESI(+)) m/e 290 (M+H)+.
Workup
- temperaturewarmed to room temperature overnight
- filtrationThe resulting precipitate was collected by filtration
- washwashed with water
- customdried in a vacuum oven
Sources & evidence
- ORD record
- ord-ca43a9798c384f1bb95abe930187b43e
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737160B2
Reaction notes
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