Water → HCID 71743833, compound

HRID 2277620Notes

Reaction equation

HRID 2277620 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:23])([CH3:22])[N:10](CC3C=CC(OC)=CC=3)[C:11](=[O:12])[C:6]2=[CH:5][CH:4]=1.O.CCOC(C)=O>CC#N>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:23])([CH3:22])[NH:10][C:11](=[O:12])[C:6]2=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 86685942HCID 86685942, compound

Product 1

HCID 71743833HCID 71743833, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To solution of 2-methoxy-6-(4-methoxy-benzyl)-7,7-dimethyl-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (0.31 g, 1.0 mmol) in CH3CN (5 mL) was added ceric ammonium nitrate (1.64 g, 3.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 hours before water and EtOAc were added into the mixture. The organic layer was separated, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by silica gel column chromatography to give the title compound (0.12 g, 63%) as a solid. MS: 193.1 (M+H+).

Workup

  1. additionwere added into the mixture
  2. customThe organic layer was separated
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e653c4d458244b84a32a20c9b5fe75f4
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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