Hydrogen Bromide → 1,6-Dibromoisoquinolin-3-amine
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10][C:11]#[N:12])[CH:3]=1.ClC(Cl)C(O)=O.[BrH:19]>>[Br:19][C:6]1[C:5]2[C:4](=[CH:3][C:2]([Br:1])=[CH:9][CH:8]=2)[CH:10]=[C:11]([NH2:12])[N:7]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
4-Bromo-2-(cyanomethyl)benzonitrile (75 g, 339 mmol) was added to 2,2-dichloroacetic acid (150 mL, 339 mmol). The resulting solution was cooled to 0° C. in an ice-water bath. HBr (27.5 g, 339 mmol) was bubbled through the cold solution until a yellow precipitate crashed out of solution resulting in a yellow slurry. HBr was bubbled through the slurry for an additional 5 minutes. The solution was allowed to warm to room temperature over 1 hour. The slurry was then re-cooled to 0° C. in an ice-water bath and diethyl ether (200 mL) was added. The mixture was stirred for 20 minutes at 5° C. The product was recovered as a yellow solid by filtration (42 g, 41%). LCMS (API-ES) m/z: 303 (M+H+).
Workup
- customresulting in a yellow slurry
- customHBr was bubbled through the slurry for an additional 5 minutes
- temperatureto warm to room temperature over 1 hour
- temperatureThe slurry was then re-cooled to 0° C. in an ice-water bath
- additiondiethyl ether (200 mL) was added
- filtrationThe product was recovered as a yellow solid by filtration (42 g, 41%)
Sources & evidence
- ORD record
- ord-c882fb89589d493284a139e18bfd129c
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897619B2
Reaction notes
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