2-Ethylphenylhydrazine Hydrochloride → 3-(4,6-Dimethoxypyrimidine-2-yl)-2-methyl-7-ethylindole

HRID 492124Notes

Reaction equation

HRID 492124 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12](=O)[CH3:13])[N:4]=1.Cl.[CH2:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24]N)[CH3:17]>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:20]3[C:19](=[C:18]([CH2:16][CH3:17])[CH:23]=[CH:22][CH:21]=3)[NH:24][C:12]=2[CH3:13])[N:4]=1

Participants

5

Reactant 2

HCID 27332092-Ethylphenylhydrazine HydrochlorideHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

Product 1

HCID 113354733-(4,6-Dimethoxypyrimidine-2-yl)-2-methyl-7-ethylindoleYield 81.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

Into a reactor were fed 2.4 g (12.2 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone, 1.7 g (9.98 m moles) of 2-ethylphenylhydrazine hydrochloride, 1.4 g (10.2 m moles) of zinc chloride and 10 ml of toluene, followed by refluxing for 2 hours with heating. After the completion of the reaction, the reaction mixture was cooled to room temperature. Thereto were added water and ethyl acetate and phase separation was made. The ethyl acetate layer was concentrated. The concentrate was subjected to silica gel column chromatography separation (developing solvent: n-hexane/ethyl acetate) to obtain 2.38 g (8.01 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methyl-7-ethylindole.

Workup

  1. customInto a reactor were fed
  2. temperatureby refluxing for 2 hours
  3. temperaturewith heating
  4. customAfter the completion of the reaction
  5. additionThereto were added
  6. customwater and ethyl acetate and phase separation
  7. concentrationThe ethyl acetate layer was concentrated
  8. customThe concentrate was subjected to silica gel column chromatography separation (developing solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7ca7b929b3404bd9a5c82ca13cd441c8
Source dataset
uspto-grants-2009_05
Patent number
US07531654B2

Reaction notes

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