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

HRID 883064

反応式

HRID 883064 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-3be33e1bec5a4f33a11bb939159fbe44
出典データセット
uspto-grants-2012_08
特許番号
US08236819B2

関連ノート

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