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

HRID 1814166노트

반응식

HRID 1814166 반응식
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]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 64796Hydrocarbostyril

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1db8a9981b184a19bbe1d535a8e3ed33
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875780B2

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