Water → HCID 178510717, compound

HRID 1577559Notes

Reaction equation

HRID 1577559 reaction equation
O[NH:2]/[C:3](/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:4]1\[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[S:8]\1.[H][H].O>C(O)(=O)C.[Pt](=O)=O>[NH2:2]/[C:3](/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:4]1\[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[S:8]\1

Participants

6

Reactant 3

HCID 962WaterHCID 178418361HCID 178418361, compound2×HCID 178516543HCID 178516543, compound

Product 1

HCID 178510717HCID 178510717, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

0.5 gm (0.00186 mol) of (E)-2-[(hydroxyamino) phenylmethylene]-benzo[b]thiophen-3(2H)-one, dissolved in 10 cc of glacial acetic acid, was catalytically hydrogenated for 21/2 hours at a hydrogen pressure of 5 bar in the presence of 0.2 gm of platinum(IV) oxide. At the end of the hydrogen uptake, the catalyst-free solution was stirred into 100 cc of water, exhaustively extracted with ether, the combined ether extracts are successively washed with water, saturated aqueous sodium bicarbonate solution and then again with water, followed by drying over sodium sulfate. The crystalline residue left behind after expelling the solvent was recrystallized twice in the presence of activated carbon from a mixture of petroleum ether and ethyl acetate (2:1). 0.37 gm (79% of theory) of egg-yellow crystals, m.p. 121°-122° C., were obtained which, on the basis of the thin-layer chromatogram, mixed melting point and IR spectrum, were found to be identical to the product obtained according to Example 1.

Workup

  1. custom2 hours
  2. extractionexhaustively extracted with ether
  3. washthe combined ether extracts are successively washed with water, saturated aqueous sodium bicarbonate solution
  4. dry with materialby drying over sodium sulfate
  5. waitThe crystalline residue left
  6. customwas recrystallized twice in the presence of activated carbon from a mixture of petroleum ether and ethyl acetate (2:1)
  7. custom0.37 gm (79% of theory) of egg-yellow crystals, m.p. 121°-122° C., were obtained which
  8. additionon the basis of the thin-layer chromatogram, mixed
  9. customobtained

Sources & evidence

ORD record
ord-584a275fb0504143834f6807ef9de6e2
Source dataset
uspto-grants-1981_09
Patent number
US04288437

Reaction notes

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