Hydrogen Bromide → 4-Bromo-3-methyl-1H-imidazo[4,5-c]pyridin-2(3H)-one
Reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([N+]([O-])=O)=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:14].[BrH:15]>>[Br:15][C:7]1[C:6]2[N:2]([CH3:1])[C:3](=[O:14])[NH:4][C:5]=2[CH:10]=[CH:9][N:8]=1Participants
3
Conditions
- Temperature
- 135 °C
Procedure
A solution of 20.0 g (103 mmol) 3-methyl-4-nitro-1H-imidazo[4,5-c]pyridin-2(3H)-one in 168 mL 48% hydrobromic acid was heated for 6 h at 135° C. An additional 33 mL of 48% hydrobromic acid was added and the reaction was stirred at 135° C. overnight. The reaction was cooled to room temperature and quenched into 1675 mL ice water. The resulting slurry was adjusted to pH 9 by the addition of 125 mL saturated aqueous ammonium hydroxide. The precipitate was filtered and washed with 200 mL water and dried in a vacuum oven at 50° C. overnight to give 17.58 g (75%) of the title product as a light yellow solids.
Workup
- temperatureThe reaction was cooled to room temperature
- customquenched into 1675 mL ice water
- additionThe resulting slurry was adjusted to pH 9 by the addition of 125 mL saturated aqueous ammonium hydroxide
- filtrationThe precipitate was filtered
- washwashed with 200 mL water
- customdried in a vacuum oven at 50° C. overnight
Sources & evidence
- ORD record
- ord-16aea41263bb4f4e976dcfe16d707b48
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163935B2
Reaction notes
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