Acetic Acid → HCID 58437502, compound

HRID 73343Notes

Reaction equation

HRID 73343 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([Cl:21])=[CH:11][C:12]([N+:18]([O-])=O)=[C:13]([CH2:15][C:16]#N)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.O>C(O)C.[Pt](=O)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][C:10]=1[Cl:21])[NH:18][CH:16]=[CH:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 58346984HCID 58346984, compound

Product 1

HCID 58437502HCID 58437502, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of (5-benzyloxy-4-chloro-2-nitrophenyl)acetonitrile (4.170 g) in ethanol (70 mL) was added platinum (IV) oxide (0.344 g) at room temperature and this mixture was stirred under a hydrogen atmosphere (30-35 psi) for 12 hours. To this reaction mixture were added acetic acid (7 mL) and water (7 mL), and this mixture was stirred under same condition for 24 hours. After this reaction mixture was replaced under argon atmosphere, the insoluble material was removed by filtration. To this filtrate was added water and this resulting mixture was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.629 g).

Workup

  1. stirringthis mixture was stirred under same condition for 24 hours
  2. customthe insoluble material was removed by filtration
  3. additionTo this filtrate was added water
  4. extractionthis resulting mixture was extracted with diethyl ether
  5. washThis organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

Sources & evidence

ORD record
ord-c6025e084e1f43e89f46a724e22c8ef9
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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