Sodium hydride → 1-[(4-Methoxyphenyl)methyl]-3,4-dihydroquinolin-2(1H)-one

HRID 2105541Notes

Reaction equation

HRID 2105541 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CN(C=O)C>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][C:2]2=[O:11])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64796HydrocarbostyrilHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 547654001-[(4-Methoxyphenyl)methyl]-3,4-dihydroquinolin-2(1H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dihydro-1H-quinolin-2-one (27 mmol) in 250 mL of anhydrous DMF is added NaH (60% in mineral oil) (30 mmol) and the mixture is stirred at room temperature for 30 minutes. 4-Methoxybenzyl chloride (30 mmol) is then added and the reaction mixture is stirred at room temperature for 2 hours. The solvent is evaporated. The residue is dissolved in 100 mL of water and extracted with CH2Cl2 three times. The combined organic layers are dried over MgSO4, filtered, and evaporated to give the crude 1-(4-methoxy-benzyl)-3,4-dihydro-1H-quinolin-2-one, which is used in the next step without further purification. Yield: 95%.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 2 hours
  2. customThe solvent is evaporated
  3. dissolutionThe residue is dissolved in 100 mL of water
  4. extractionextracted with CH2Cl2 three times
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d4a0640bbe3f492c9a668655c39a8e72
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

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