7,8-Dihydro-2-(phenylmethoxy)-5(6H)-quinolinone → HCID 10061627, compound

HRID 1586980Notes

Reaction equation

HRID 1586980 reaction equation
[CH3:1][Mg]Br.[O:4]=[C:5]1[CH2:14][CH2:13][CH2:12][C:11]2[N:10]=[C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:8]=[CH:7][C:6]1=2>C1(C)C=CC=CC=1>[OH:4][C:5]1([CH3:1])[CH2:14][CH2:13][CH2:12][C:11]2[N:10]=[C:9]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:8]=[CH:7][C:6]1=2

Participants

4

Reactant 2

HCID 104449777,8-Dihydro-2-(phenylmethoxy)-5(6H)-quinolinoneHCID 178418573HCID 178418573, compound

Product 1

HCID 10061627HCID 10061627, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methylmagnesium bromide (3.0M in diethyl ether, 47 ml) was added dropwise to a solution of 5,6,7,8-tetrahydro-5-oxo-2(phenylmethoxy)quinoline (29.6 g) and toluene (1 l) at 0° C. The reaction mixture was allowed to warm to room temperature, with stirring. The redaction mixture was then quenched with saturated ammonium chloride solution, the layers were separate, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to provide 31.7 g (92.0%) of product.

Workup

  1. customThe redaction mixture was then quenched with saturated ammonium chloride solution
  2. customthe layers were separate
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7df3cb4e04364ccea154849a04e2794c
Source dataset
uspto-grants-1993_06
Patent number
US05216164

Reaction notes

Loading…