Toluene → 5-Chloro-3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole

HRID 492130

반응식

HRID 492130 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.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30]N)=[CH:26][CH:25]=1.C(OCC)(=O)C>[Cl-].[Zn+2].[Cl-].O>[Cl:23][C:24]1[CH:29]=[C:28]2[C:27](=[CH:26][CH:25]=1)[NH:30][C:19]([CH3:20])=[C:18]2[C:12]1[N:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]([O:9][CH3:8])[N:11]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

생성물 1

HCID 178567665-Chloro-3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole수율 84%

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 7.9 g (44 m moles) of 4-chlorophenylhydrazine hydrochloride. Thereto was added 6.54 g (48 m moles) of zinc chloride. Refluxing was made for 2 hours with heating. The reaction mixture was allowed to cool. Then, ethyl acetate and water were added to dissolve the whole reaction mixture. The organic layer was washed with water, separated, and dried over Glauber's salt. The resulting organic layer was concentrated under reduced pressure using a rotary evaporator to obtain an orange solid. The solid was washed with isopropyl ether to obtain 10.2 g (33.7 m moles) of 5-chloro-3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole. Yield: 84% Melting point: 179 to 181° C.

후처리

  1. temperatureRefluxing
  2. temperaturewith heating
  3. temperatureto cool
  4. dissolutionto dissolve
  5. customthe whole reaction mixture
  6. washThe organic 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. customa rotary evaporator
  11. customto obtain an orange solid
  12. washThe solid was washed with isopropyl ether

출처 및 근거

ORD 기록
ord-ead58d8be5a34a75b626e3cf4bce05b5
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531654B2

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