HCID 57092295, compound → HCID 53975106, compound

HRID 259735Notes

Reaction equation

HRID 259735 reaction equation
[CH:1]([C:4]([CH3:22])([N:7]1[C:11](=[O:12])[CH:10]2[CH2:13][CH2:14][C:15]3[N:16]([CH3:20])[CH:17]=[CH:18][C:19]=3[CH:9]2[C:8]1=[O:21])[C:5]#[N:6])([CH3:3])[CH3:2]>ClC1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH:1]([C:4]([CH3:22])([N:7]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][C:15]3[N:16]([CH3:20])[CH:17]=[CH:18][C:19]=3[C:9]=2[C:8]1=[O:21])[C:5]#[N:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57092295HCID 57092295, compound

Product 1

HCID 53975106HCID 53975106, compoundYield 11.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 7964ChlorobenzeneSolvent

Procedure

Activated manganese dioxide (27.0 g, 0.310 mol) is added to a solution of 3,3a,4,5,6,8b-hexahydro-α-isopropyl-α,6-dimethyl-1,3-dioxobenzo-[1,2-b:3,4-c']dipyrrole-2(1H)-acetonitrile (51.3 g, 0.167 mol) in chlorobenzene. The reaction mixture is stirred overnight at reflux temperature, cooled and filtered twice through diatomaceous earth with methylene chloride. The filtrate is concentrated in vacuo to a black oil which is flash chromatographed twice with methylene chloride then hexanes:methylene chloride to afford a yellow solid (5.50 g, 11.6%). Recrystallization from hexanes:methylene chloride afforded the title product, mp 123°-128° C.

Workup

  1. temperatureat reflux temperature
  2. temperaturecooled
  3. filtrationfiltered twice through diatomaceous earth with methylene chloride
  4. concentrationThe filtrate is concentrated in vacuo to a black oil which
  5. customchromatographed twice with methylene chloride

Sources & evidence

ORD record
ord-d107c5c5cc0643f6aa1d88b1d9d1df78
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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