2-Acetylpyridine → 2,3,5,6-tetramethyl-N-(1-pyridin-2-ylethylidene)-benzene-1,4-diamine

HRID 17786

反応式

HRID 17786 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[CH3:10][C:11]1[C:16]([CH3:17])=[C:15]([NH2:18])[C:14]([CH3:19])=[C:13]([CH3:20])[C:12]=1[NH2:21]>C1(C)C=CC=CC=1.C(O)=O>[CH3:17][C:16]1[C:11]([CH3:10])=[C:12]([NH2:21])[C:13]([CH3:20])=[C:14]([CH3:19])[C:15]=1[N:18]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]

参加物

5

反応物 2

HCID 142862-AcetylpyridineHCID 765482,3,5,6-Tetramethyl-1,4-phenylenediamine

生成物 1

HCID 860835722,3,5,6-tetramethyl-N-(1-pyridin-2-ylethylidene)-benzene-1,4-diamine収率 445.9%

試薬・触媒・溶媒 2

HCID 284Formic Acid触媒HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 2-acetylpyridine (0.30 ml, 0.26 mmol) and 2,3,5,6-tetramethyl-benzene-1,4-diamine (0.60 g, 0.37 mmol, 1.4 eq.) in toluene (2 ml) was added 2 drops of formic acid. The suspension was heated for three days at 50° C. The dark reddish suspension was cooled, filtered and the residue washed with cold toluene. The filtrate was evaporated, dissolved in chloroform (2 ml) and cooled to −78° C. for 0.5 hours before being filtered. Hexane was added to the filtrate and all volatiles were removed under reduced pressure to give 2,3,5,6-tetramethyl-N-(1-pyridin-2-ylethylidene)-benzene-1,4-diamine as a brown solid (0.31 g, 45%).

後処理

  1. temperatureThe dark reddish suspension was cooled
  2. filtrationfiltered
  3. washthe residue washed with cold toluene
  4. customThe filtrate was evaporated
  5. dissolutiondissolved in chloroform (2 ml)
  6. temperaturecooled to −78° C. for 0.5 hours
  7. filtrationbefore being filtered
  8. additionHexane was added to the filtrate
  9. customall volatiles were removed under reduced pressure

出典と根拠

ORDレコード
ord-8ce7c26fc9964d679eb3ceefa671fdef
出典データセット
uspto-grants-2010_06
特許番号
US07741240B2

関連ノート

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