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M-Cresol → N-(4-methylphenyl)-4-methoxy-6-(3-methylphenoxy)-2-pyridine carboxamide

HRID 1250490
ノート
印刷プレビュー

反応式

HRID 1250490 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23](Br)[N:22]=2)=[O:20])=[CH:14][CH:13]=1>CN(C=O)C.CCCCCC.[Cu](Cl)Cl>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[N:22]=2)=[O:20])=[CH:16][CH:17]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 342M-CresolHCID 24758Sodium hydrideHCID 18326207N-(4-methylphenyl)-6-bromo-4-methoxy-2-pyridine carboxamide

生成物 1

HCID 15906600N-(4-methylphenyl)-4-methoxy-6-(3-methylphenoxy)-2-pyridine carboxamide

試薬・触媒・溶媒 3

HCID 24014Cupric Chloride触媒HCID 6228
Dimethylformamide
溶媒
HCID 8058Hexane溶媒

反応条件

温度
100 °C

実験手順

0.45 g (0.0019×2.2 mol) of 3-methyl phenol was dissolved in about 10 ml of DMF. The obtained solution was further mixed with 0.15 g (ca. 60% in mineral oil; 0.0019×2.0 mol) of NaH and then with 0.60 g (0.0019 mol) of N-(4-methylphenyl)-6-bromo-4-methoxy-2-pyridine carboxamide. After adding 0.19 g (0.0019×1.0 mol) of copper chloride (I), the solution was stirred at about 100° C. for about 4 hours, and then allowed to stand for cooling to room temperature. After the reaction solution was distributed in hexane-saturated sodium bicarbonate water, the organic phase of the solution was washed with saturated brine and dried with anhydrous sodium sulfate, followed by concentration thereof. Thereafter, the concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

後処理

  1. temperaturefor cooling to room temperature
  2. washthe organic phase of the solution was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationfollowed by concentration
  5. customThereafter, the concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-4e8cf4c5f1fb4848b7d607c7c9bd8232
出典データセット
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06339045B1

反応ノート

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