Sodium hydride → Methyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-1-yl)acetate

HRID 1814166ノート

反応式

HRID 1814166 の反応式
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[NH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:19]>C1COCC1>[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:19]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 64796Hydrocarbostyril

生成物 1

HCID 21349898Methyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-1-yl)acetate収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl bromoacetate (5.72 g, 37.4 mmol) was slowly added to a stirred solution of sodium hydride (1.5 g, 37.4 mmol) and 3,4-dihydro-2 (1H)quinolinone (5.0 g, 34 mmol) in THF. The mixture was stirred at RT for 3 h. After removing the solvent, the residue was diluted with water and ether. The layers were separated and the aqueous layer was extracted with ether (3×50 mL). The combined organics were dried with MgSO4 and condensed to afford the desired product, compound 49A (7.06 g, 95%) as a yellow solid. MS m/z 220 (M+1). Step 2. Preparation of (6-Chlorosulfonyl-2-oxo-3,4-dihydro-2H-quinolin-1-yl) acetic acid methyl ester (Compound 49B).

後処理

  1. customAfter removing the solvent
  2. additionthe residue was diluted with water and ether
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (3×50 mL)
  5. dry with materialThe combined organics were dried with MgSO4 and condensed

出典と根拠

ORDレコード
ord-1db8a9981b184a19bbe1d535a8e3ed33
出典データセット
uspto-grants-2005_04
特許番号
US06875780B2

反応ノート

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