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

HRID 1453646노트

반응식

HRID 1453646 반응식
[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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 64796Hydrocarbostyril2회HCID 122764491-Bromo-3-(bromomethyl)-5-methoxybenzene

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a0bf169bfbea47dbbb490f8183a65566
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476675B2

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