1-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)prop-2-en-1-one → 1-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)propan-1-one

HRID 1382841Notes

Reaction equation

HRID 1382841 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH:9]=[CH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2>CO>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2

Participants

3

Reactant 1

HCID 538459351-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)prop-2-en-1-one

Product 1

HCID 137856631-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)propan-1-oneYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 200 mg of the product of Step A in 10 ml of methanol was hydrogenated in the presence of palladized activated charcoal at room temperature until absorption ceased and was then filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica. Elution with a 6-3-1 cyclohexane-dichloromethane-triethylamine mixture yielded 143 mg of 1-(2-hydroxyphenyl)-3-(1H-indol-4-yl)-1-propanone melting at ≃143° C.

Workup

  1. customwas hydrogenated in the presence of palladized activated charcoal at room temperature until absorption
  2. filtrationwas then filtered
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was chromatographed over silica
  5. washElution with a 6-3-1 cyclohexane-dichloromethane-triethylamine mixture

Sources & evidence

ORD record
ord-97648cff80d94f8283056914e3f47957
Source dataset
uspto-grants-1989_02
Patent number
US04808609

Reaction notes

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