Iodoethane → 7-Bromo-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one

HRID 883064

반응식

HRID 883064 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[CH3:15].[OH-].[K+].[CH2:18](I)[CH3:19]>CS(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])([CH3:14])[CH2:7][C:8](=[O:12])[N:9]2[CH2:18][CH3:19])=[CH:4][C:3]=1[CH3:15]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 219664237-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one

생성물 1

HCID 219664867-Bromo-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one수율 88.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

A solution of 8.5 g of 7-bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one (31.7 mmol), prepared according to WO 03/075924, in 15 mL dry DMSO was added to a prestirred solution of crushed potassium hydroxide (3.56 g, 63.4 mmol) in 15 mL of dry DMSO, followed by addition of 7.68 mL (95.2 mmol) of ethyl iodide. The reaction was stirred overnight before quenching with 100 mL of water and extracted with dichloromethane (3×150 mL), the extracts were dried with sodium sulfate, filtered, stripped and purified via flash chromatography (5% EtOAc/hexanes) to afford 8.3 g of product (88%) as a white solid. MS (electrospray): mass calculated for C14H18BrNO, 295.06; m/z found 296, [M+H]+.

후처리

  1. custombefore quenching with 100 mL of water
  2. extractionextracted with dichloromethane (3×150 mL)
  3. dry with materialthe extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. custompurified via flash chromatography (5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-3be33e1bec5a4f33a11bb939159fbe44
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236819B2

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