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

HRID 1785385

Reaction equation

HRID 1785385 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e8396653ac5649f38ff675384758ab7f
Source dataset
uspto-grants-2009_03
Patent number
US07504503B2

Linked notes

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