Methanol → 5-Bromo-6-hydroxy-7-methyl-quinoline

Temperature

0 °C

To the solution of 5-bromo-6-methoxy-7-methylquinoline (6.5 g, 25.8 mmol) in DCM (150 mL) was added BBr3 slowly (77.3 mL, 1.0 M in DCM, 77.3 mmol). The mixture was stirred for 3 hours and cooled to 0° C. Methanol (40 mL) was added slowly and the mixture was stirred for 20 minutes. The solvents were removed under reduced pressure. The solid was dissolved in methanol (100 mL) and was treated with 1.0 N sodium hydroxide solution (50 mL) (pH ˜12). The mixture was stirred for 12 hours and acetic acid was added to adjust pH to between 4-5. The mixture was filtered and washed with water. The gray solid was dried under reduced pressure to give 5-bromo-7-methylquinolin-6-ol. LCMS-ESI+ (m/z): 238.2, 240.1 (M+H)+, 236.1, 238.0 (M−H).

1. stirringthe mixture was stirred for 20 minutes
2. customThe solvents were removed under reduced pressure
3. dissolutionThe solid was dissolved in methanol (100 mL)
4. additionwas treated with 1.0 N sodium hydroxide solution (50 mL) (pH ˜12)
5. stirringThe mixture was stirred for 12 hours
6. additionacetic acid was added
7. filtrationThe mixture was filtered
8. washwashed with water
9. customThe gray solid was dried under reduced pressure

ORD record

ord-2433334a4341403a82128b8a22a1ce90

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376392B2