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

HRID 1195157Notes

Reaction equation

HRID 1195157 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 (1l) at 0° C. The reaction mixture was allowed to warm to room temperature, with stirring. The reaction mixture was then quenched with saturated ammonium chloride solution, the layers were separated, 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 reaction mixture was then quenched with saturated ammonium chloride solution
  2. customthe layers were separated
  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-99c18dc6a5b34c158cfbf78a21b85efd
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

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