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

HRID 1453646ノート

反応式

HRID 1453646 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a0bf169bfbea47dbbb490f8183a65566
出典データセット
uspto-grants-2009_01
特許番号
US07476675B2

反応ノート

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