Sodium hydride → 4-(3-Bromo-5-methoxy-benzyl)-3,4-dihydro-1H-quinoline-2-one

HRID 1453646Notes

Reaction equation

HRID 1453646 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+].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1)[CH2:18]Br>CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1)[CH2:18][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1][C:2](=[O:11])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64796Hydrocarbostyril2×HCID 122764491-Bromo-3-(bromomethyl)-5-methoxybenzene

Product 1

HCID 223242594-(3-Bromo-5-methoxy-benzyl)-3,4-dihydro-1H-quinoline-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dihydro-2(1H)-quinolinone was purchased from Aldrich Chemical Co. (Cat. No. 41,593-6) and used without purification in this step. 0.45 grams of 3,4-dihydro-2(1H)-quinolinone (3.0 mmole) was dissolved in 15 ml dimethylformamide and cooled in an ice bath. 0.2 grams (4.5 mmole) of sodium hydride (60% wt. in oil ) was added to this solution, and after 5 minutes 0.84 grams 3-bromo-5-methoxy-benzylbromide (3 mmol) was added thereto all at once. The mixture was stirred at ice bath temperature for 1 hour and then quenched by addition of 1% hydrochloric acid. The reaction mix was extracted with ethyl acetate, which was evaporated under reduced pressure to give an oil, which was chromatographed with medium pressure eluting using 10% ethyl acetate in hexanes to yield 0.8 grams of solid 4-(3-bromo-5-methoxy-benzyl)-3,4-dihydro-1H-quinoline-2-one.

Workup

  1. custom41,593-6) and used without purification in this step
  2. temperaturecooled in an ice bath
  3. customquenched by addition of 1% hydrochloric acid
  4. additionThe reaction mix
  5. extractionwas extracted with ethyl acetate, which
  6. customwas evaporated under reduced pressure
  7. customto give an oil, which
  8. customwas chromatographed with medium pressure
  9. washeluting

Sources & evidence

ORD record
ord-a0bf169bfbea47dbbb490f8183a65566
Source dataset
uspto-grants-2009_01
Patent number
US07476675B2

Reaction notes

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