3',4',5'-Trimethoxyacetophenone → (E)-3-(6-Nitroindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one

HRID 618112Notes

Reaction equation

HRID 618112 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N+:16]([C:19]1[CH:27]=[C:26]2[C:22]([C:23]([CH:28]=O)=[CH:24][NH:25]2)=[CH:21][CH:20]=1)([O-:18])=[O:17]>>[N+:16]([C:19]1[CH:27]=[C:26]2[C:22]([C:23](/[CH:28]=[CH:14]/[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:15])=[CH:24][NH:25]2)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

3

Reactant 2

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 52100766-nitro-1H-indole-3-carbaldehyde

Product 1

HCID 21850294(E)-3-(6-Nitroindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-oneYield 1.1%

Procedure

Substantially the same procedure as in Example 21 was repeated using 3',4',5'-trimethoxyacetophenone (1.25 g) and 6-nitroindole-3-carboxaldehyde (1.13 g) except that the obtained product was further purified by preparative HPLC, that the eluting solution was cooled, and that the precipitated crystals were collected by filtration, to give Compound 34 (26 mg).

Workup

  1. customwas further purified by preparative HPLC, that the eluting solution
  2. temperaturewas cooled
  3. filtrationthat the precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-b5d594092288441b837e6e6e11286f03
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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