Water → 6-bromo-1-(4-methoxybenzyl)quinolin-2(1H)-one

HRID 1696539Notes

Reaction equation

HRID 1696539 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.[OH-].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:8]2[C:9]3[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]2=[O:12])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 123789436-Bromoquinolin-2(1H)-one

Product 1

HCID 672720826-bromo-1-(4-methoxybenzyl)quinolin-2(1H)-oneYield 87.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

6-Bromoquinolin-2(1H)-one (4.0 g, 18 mmol), 4-methoxybenzyl chloride (3.6 g, 23 mmol), and tetrabutylammonium bromide (1.2 g, 3.6 mmol) were dissolved in PhMe (200 mL) and then KOH (powder, 1.8 g, 32 mmol) was added into the reaction mixture. The reaction mixture was stirred at RT for 4 h, then poured into H2O and extracted with EtOAc (3×50 mL). The organic layer was washed with H2O, dried (Na2SO4), and concentrated. Trituration with hexane, followed by collection of the solids yielded 1-(4-methoxybenzyl)-6-bromoquinolin-2(1H)-one (5.4 g, 87% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.70 (d, J=2.4 Hz, 1H), 7.66 (d, J=9.6 Hz, 1H), 7.52 (dd, J=2.0, and 8.8 Hz, 1H), 7.19 (d, J=9.2 Hz, 1H), 7.16 (d, J=8.8 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 6.83 (d, J=9.4 Hz, 1H), 5.48 (brs, 2H), 3.78 (s, 3H), 1.36 (s, 12H); LC-MS (EI) m/z: 344.0 (M+H+).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe organic layer was washed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customTrituration with hexane, followed by collection of the solids

Sources & evidence

ORD record
ord-730ce84309e2487687fe902a0ff5d2ea
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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