Benzyl Bromide → 7,8-Dihydro-2-(phenylmethoxy)-5(6H)-quinolinone

HRID 1821093Notes

Reaction equation

HRID 1821093 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][C:2]1=[O:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:13]([O:12][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:11])[CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2674502-Hydroxy-7,8-dihydro-5(6H)-quinolinone

Product 1

HCID 104449777,8-Dihydro-2-(phenylmethoxy)-5(6H)-quinolinoneYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7,8-dihydro-1H,6H-quinoline-2,5-dione (20.4 g, 125.0 mmoL), benzyl bromide (17.8 mL, 150 mmoL) and 20.8 g, 75 mmoL) in toluene (250 mL) was stirred at room temperature for 3 days under the protection from light. The reaction was stopped, filtered through celite and rinsed with a mixture of methylene chloride and methanol. The filtrate was concentrated and trituated in petroleum ether (150 mL). Filtration of the mixture provided the desired product (29.4 g, 92%).

Workup

  1. filtrationfiltered through celite
  2. washrinsed with a mixture of methylene chloride and methanol
  3. concentrationThe filtrate was concentrated
  4. filtrationFiltration of the mixture

Sources & evidence

ORD record
ord-04894738ec954b35b3d7e61e2b6cf196
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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