HCID 19592667, compound → HCID 19592398, compound

HRID 613504Notes

Reaction equation

HRID 613504 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]2)=[O:5]>O1CCOCC1.[Pt](=O)=O>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]2)=[O:5]

Participants

4

Reactant 1

HCID 19592667HCID 19592667, compound

Product 1

HCID 19592398HCID 19592398, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-3-((E)-2-ethoxycarbonylvinyl)quinoline (40 mg) and platinum (IV) oxide (5 mg) in dioxane (1 ml) was stirred for 3 hours at ambient temperature under hydrogen atmosphere. Insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was purified by preparative thin layer chromatography (ethyl acetate-n-hexane) to give 8-(2,6-dichlorobenzoylamino)-3-(2-ethoxycarbonylethyl)quinoline (16 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative thin layer chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-0ff8a376a0984408839de3ccf12c8109
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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