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

HRID 1033503Notes

Reaction equation

HRID 1033503 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[NH:7][C:6](=[O:12])[CH:5]=[CH:4][C:3]1=2.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(=O)([O-])[O-].[Ag+2].C1(C)C=CC=CC=1>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

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

Product 1

HCID 104449777,8-Dihydro-2-(phenylmethoxy)-5(6H)-quinolinoneYield 89%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone (33.0 g), silver carbonate (35.0 g), benzyl bromide (44.4 g), and toluene (400 ml) was stirred at room temperature for 72 hrs. The mixture was filtered and the filtrate was concentrated. Trituration of the residue with petroleum ether gave 45.6 g (83%) of product.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9a4cb8125e774473a9f8691548d992e6
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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