(+/-)-2a,5-Dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione → Pyrrolo[4,3,2-de]quinoline-2,4(1H,5H)-dione

HRID 551006Notes

Reaction equation

HRID 551006 reaction equation
[NH:1]1[C:11]2[C:12]3[CH:3]([CH2:4][C:5](=[O:13])[NH:6][C:7]=3[CH:8]=[CH:9][CH:10]=2)[C:2]1=[O:14]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[NH:1]1[C:11]2[C:12]3[C:3](=[CH:4][C:5](=[O:13])[NH:6][C:7]=3[CH:8]=[CH:9][CH:10]=2)[C:2]1=[O:14]

Participants

4

Reactant 1

HCID 57663743(+/-)-2a,5-Dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione

Product 1

HCID 57663757Pyrrolo[4,3,2-de]quinoline-2,4(1H,5H)-dione

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (±)-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione from Step C (200 mg, 1.06 mmol), and manganese (IV) oxide (185 mg, 2.13 mmol) was heated in toluene (3 mL) at 110° C. for 1 h. The mixture was filtered through a pad of Celite, washing with CH2Cl2:MeOH, and the filtrate was concentrated in vacuo to give the title compound. MS: m/z=187 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing with CH2Cl2
  3. concentrationMeOH, and the filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cc786cdc1b114db4b9f4df0fd5523b83
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

Loading…