Sulfuric Acid → HCID 19097339, compound

HRID 486061Notes

Reaction equation

HRID 486061 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.[CH3:12][CH2:13][CH2:14][C:15](=O)[CH2:16][CH2:17][CH3:18].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:13]([C:14]1[C:8]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:9]=2)[NH:10][C:15]=1[CH2:16][CH2:17][CH3:18])[CH3:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 312464-HeptanoneHCID 516892Sodium BicarbonateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 19097339HCID 19097339, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 4-methoxyphenyl hydrazine hydrochloride (3.0 g), 4-heptanone (1.94 g), and sulfuric acid (1.3 ml) in ethanol (10 ml) was stirred at 10° C. for 3 hours. The cooled mixture was poured into aqueous sodium bicarbonate solution, such that the pH was adjusted to 9. The solution was extracted with ethyl acetate, the organic layer separated, washed with water, dried over magnesium sulfate, and concentrated in vacuo. The crude product was chromatographed on silica gel using 25%-ethyl acetate in n-hexanes as eluent to yield 3-ethyl-5-methoxy-2-propylindole (3.22 g).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. customthe organic layer separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was chromatographed on silica gel using 25%-ethyl acetate in n-hexanes as eluent

Sources & evidence

ORD record
ord-caf00ededb83482591a24e4f44f6c9c3
Source dataset
uspto-grants-1994_03
Patent number
US05290788

Reaction notes

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