Sulfuric Acid → 5-Benzyloxy-3-(3-chloro-phenyl)-2-methyl-1H-indole

HRID 66820

Reaction equation

HRID 66820 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16]N)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH2:25][C:26](=O)[CH3:27])[CH:22]=[CH:23][CH:24]=1.S(=O)(=O)(O)O>C(O)C>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]2[C:13](=[CH:12][CH:11]=1)[NH:16][C:26]([CH3:27])=[C:25]2[C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[CH:20]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 27340971-(3-Chlorophenyl)propan-2-oneHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Product 1

HCID 205292015-Benzyloxy-3-(3-chloro-phenyl)-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 11.7 g (47 m mole) of 4-benzyloxyphenylhydrazine-hydrochloride and 6.39 g (38 m mole) of (3-chlorophenyl)-acetone was dissolved in 35 ml of absolute ethanol, and after addition of 2.7 ml of concentrated sulfuric acid the mixture was refluxed for five hours. After the ethanol was distilled off, the residue was mixed with water and extracted with chloroform. The extracts were dried over sodium sulfate and evaporated. The evaporation residue was purified by chromatography on silicagel by using toluene as solvent.

Workup

  1. temperaturewas refluxed for five hours
  2. distillationAfter the ethanol was distilled off
  3. additionthe residue was mixed with water
  4. extractionextracted with chloroform
  5. dry with materialThe extracts were dried over sodium sulfate
  6. customevaporated
  7. customThe evaporation residue was purified by chromatography on silicagel

Sources & evidence

ORD record
ord-f34ce889d3be4b0e8cb3c4cfd7a91c36
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Linked notes

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