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

HRID 1785383Notes

Reaction equation

HRID 1785383 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.[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

Participants

7

Reactant 4

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

Product 1

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

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 7.9 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.

Workup

  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

Sources & evidence

ORD record
ord-ec94b331c19a429789e4a3c859c7e14c
Source dataset
uspto-grants-2009_03
Patent number
US07504503B2

Reaction notes

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