Benzyl Bromide → 6-(Benzyloxy)-3,4-dihydroquinolin-2(1H)-one

HRID 490693Notes

Reaction equation

HRID 490693 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CN(C=O)C>[CH2:25]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)[C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 445658826-(Benzyloxy)-3,4-dihydroquinolin-2(1H)-oneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-hydroxy-3,4-dihydro-1H-quinolin-2-one (2.93 g, 17.9 mmol) in DMF (20 mL) is treated with K2CO3 (4.97 g) and BnBr (4.61 g, 26.9 mmol). The suspension is stirred at room temperature for 4 hours and quenched with water (100 mL). The mixture is extracted with EtOAc (50 mL×2) and the combined organics are dried (Na2SO4), concentrated, and purified on silica gel chromatography column with 30-60% EtOAc/Hexanes to yield the title compound (4.40 g, 97%).

Workup

  1. customquenched with water (100 mL)
  2. extractionThe mixture is extracted with EtOAc (50 mL×2)
  3. dry with materialthe combined organics are dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified on silica gel chromatography column with 30-60% EtOAc/Hexanes

Sources & evidence

ORD record
ord-f44a10d63f734f45995312b128123632
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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