Carbon Dioxide → 4-Dimethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid

HRID 1531639ノート

反応式

HRID 1531639 の反応式
Br[C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:3]=1.C([Li])CCC.[C:27](=[O:29])=[O:28]>C(OCC)C>[CH3:9][N:8]([CH3:10])[C:6]1[CH:5]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:3]=[C:2]([C:27]([OH:29])=[O:28])[CH:7]=1

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 212498292-Bromo-N,N-dimethyl-6-[3-(trifluoromethyl)phenoxy]pyridin-4-amineHCID 178418339Butyllithium

生成物 1

HCID 212498284-Dimethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

2-bromo-4-dimethylamino-6-[3-(trifluoromethyl)phenoxy] pyridine (5.00 g, 0.0138 mol) was dissolved in about 200 ml of diethyl ether. While cooling in a dry ice-acetone bath in an argon atmosphere, the obtained solution was mixed with n-butyl lithium [9.2 ml (ca. 1.66 M in hexane solution), 0.0138×1.1 mol], and then stirred for about 10 minutes. After the interior of the reactor was replaced with a carbon dioxide gas, the solution was removed from the bath and stirred at room temperature for about one hour. The reaction solution was mixed with about 15 ml of a 4 N aqueous hydrochloric acid solution, distributed in ethyl acetate-water, and then washed with saturated brine. The organic phase separated from the solution was dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

後処理

  1. temperatureWhile cooling in a dry ice-acetone bath in an argon atmosphere
  2. customthe solution was removed from the bath
  3. stirringstirred at room temperature for about one hour
  4. additionThe reaction solution was mixed with about 15 ml of a 4 N aqueous hydrochloric acid solution
  5. washwashed with saturated brine
  6. customThe organic phase separated from the solution
  7. dry with materialwas dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-583288195ada4096a3ca7843d7acfb95
出典データセット
uspto-grants-2001_03
特許番号
US06200933B1

反応ノート

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