Toluene → 3-(4,6-Dimethoxypyrimidine-2-yl)-5-methoxy-2-methylindole

HRID 492132

반응식

HRID 492132 반응식
C1(C)C=CC=CC=1.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[N:13]=[C:12]([CH2:18][C:19](=O)[CH3:20])[N:11]=1.Cl.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31]N)=[CH:27][CH:26]=1.C(OCC)(=O)C>[Cl-].[Zn+2].[Cl-].O>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[N:13]=[C:12]([C:18]2[C:29]3[C:28](=[CH:27][CH:26]=[C:25]([O:24][CH3:23])[CH:30]=3)[NH:31][C:19]=2[CH3:20])[N:11]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

생성물 1

HCID 178567633-(4,6-Dimethoxypyrimidine-2-yl)-5-methoxy-2-methylindole수율 67%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 962Water용매

실험 절차

To 80 ml of toluene were added 8.0 g (40 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 7.7 g (44 m moles) of 4-metoxyphenylhydrazine hydrochloride. Thereto was added 6.0 g (44 m moles) of zinc chloride. Refluxing was made for 2 hours with heating. The reaction mixture was allowed to cool. Thereto were added ethyl acetate and water to dissolve the whole reaction mixture. The oily layer was washed with water, separated and dried over Glauber's salt. The resulting organic layer was concentrated under reduced pressure using an rotary evaporator to obtain, as an orange solid, 8.0 g (26.7 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-5-methoxy-2-methylindole. Yield: 67% Recrystallization from toluene was made.

후처리

  1. temperatureRefluxing
  2. temperaturewith heating
  3. temperatureto cool
  4. dissolutionto dissolve
  5. customthe whole reaction mixture
  6. washThe oily layer was washed with water
  7. customseparated
  8. dry with materialdried over Glauber's salt
  9. concentrationThe resulting organic layer was concentrated under reduced pressure
  10. customan rotary evaporator

출처 및 근거

ORD 기록
ord-f874ce1897784008bb6ea42e66a46d75
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531654B2

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