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

HRID 17786

반응식

HRID 17786 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 284Formic Acid촉매HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-8ce7c26fc9964d679eb3ceefa671fdef
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741240B2

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