Acetic Acid → N-benzyl-6-chloro-4-o-tolyl-nicotinamide

HRID 379421

반응식

HRID 379421 반응식
[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[N:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([CH3:26])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Mg]Cl.C(O)(=O)C>C1COCC1.O.O.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Mn+3]>[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[C:15]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH3:26])=[CH:14][C:13]([Cl:16])=[N:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 857488N-Benzyl-6-chloro-nicotinamideHCID 178424304HCID 178424304, 화합물

생성물 1

HCID 12167314N-benzyl-6-chloro-4-o-tolyl-nicotinamide수율 89.1%

시약·촉매·용매 2

HCID 12416832Manganese triacetate dihydrate촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of 0.5 g (2.0 mMol) N-benzyl-6-chloro-nicotinamide in 5.0 ml THF was added over 25 minutes to 10.1 ml (10.1 mMol) of o-tolylmagnesium chloride solution (1M in THF) cooled to 0° C. After 2.5 hours stirring at room temperature, the reaction mixture was cooled again to 0° C. and 4.0 ml acetic acid were added over 15 minutes followed by 1.1 g (4.1 mMol) manganese triacetate dihydrate. After stirring for 1 hour at room temperature, the reaction mixture was filtered and the filtrate was poured onto 20 ml deionized water. Sodium bicarbonate was added portionwise to bring the pH to 7 and the phases were separated. The aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with water, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (eluent ethyl acetate/n-hexane 2:1) to yield 0.6 g (88%) N-benzyl-6-chloro-4-o-tolyl-nicotinamide as an orange resin.

후처리

  1. temperaturethe reaction mixture was cooled again to 0° C.
  2. stirringAfter stirring for 1 hour at room temperature
  3. filtrationthe reaction mixture was filtered
  4. additionthe filtrate was poured onto 20 ml
  5. additionSodium bicarbonate was added portionwise
  6. customthe phases were separated
  7. extractionThe aqueous layer was extracted with dichloromethane
  8. washThe combined organic extracts were washed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customThe residue was purified by flash chromatography (eluent ethyl acetate/n-hexane 2:1)

출처 및 근거

ORD 기록
ord-9c1004844e1743f5ab97ad94b3f4675d
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297375B1

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