Acetic Acid → HCID 58437502, compound

HRID 1258199Notes

Reaction equation

HRID 1258199 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-a10cea3a07ac4a7cb125352d5d30399f
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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