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 (5.0 g). 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-7bac8e3398b043f1b0b7d5374a40c5b2

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296758B2