HCID 69915989, compound → HCID 73990358, compound

HRID 1166099Notes

Reaction equation

HRID 1166099 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH:12]=[CH:13][CH2:14][OH:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1>CC(C)=O.O=[Mn]=O>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH:12]=[CH:13][CH:14]=[O:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 69915989HCID 69915989, compound

Product 1

HCID 73990358HCID 73990358, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of the compound from step C (185 mg, 0.92 mmol) and MnO2 (1.60 g, 18.40 mmol) in acetone (15 mL) was heated to reflux for 1 h. The cooled reaction mixture was filtered through Celite and the filtrate was concentrated. Purification by chromatography (SiO2, 2:1 hexane/ethyl acetate) yielded 78 mg (43%) of the title compound. MS 200 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through Celite
  5. concentrationthe filtrate was concentrated
  6. customPurification by chromatography (SiO2, 2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3d6062b708ce43ba92e6375e571fad32
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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