Water → 4-(6-Hydroxy-3-methylquinolin-2-yl)benzoic acid

HRID 628851Notes

Reaction equation

HRID 628851 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=1)[C:7]([CH3:23])=[CH:6]2.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=1)[C:7]([CH3:23])=[CH:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 66980055Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate

Product 1

HCID 569607734-(6-Hydroxy-3-methylquinolin-2-yl)benzoic acidYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate (37 mg, 0.121 mmol) was dissolved in 2 mL of DCM and BBr3 (150 μL) was added. The mixture was stirred at room temperature for 1 day followed by addition of 10 mL of H2O. The solution was stirred vigorously for 1 h followed by filtration of the solids. The solids were washed with H2O and dried in vacuo to yield 9.5 mg (28% yield) of Compound 1. 1H NMR (DMSO-d6, 400 MHz): δ 8.37 (s, 1H), 8.10 (d, 2H), 7.94 (d, 1H), 7.78 (d, 2H), 7.42-7.39 (dd, 1H), 7.24-7.23 (d, 1H), 2.43 (s, 3H). MS (ESI): m/z 280.10 [M+H]+.

Workup

  1. stirringThe solution was stirred vigorously for 1 h
  2. filtrationfollowed by filtration of the solids
  3. washThe solids were washed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8bdbda1b77db418194382741244cf99b
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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