HCID 22401507, compound → HCID 483550, compound

HRID 260483Notes

Reaction equation

HRID 260483 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][CH:32]=1)[CH2:7][NH:8][C:9]([C:11]1[NH:12][C:13]2[C:18]([C:19]=1[S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[CH:17][C:16]([Cl:29])=[CH:15][CH:14]=2)=[O:10])([O-])=O.[H][H]>O1CCCC1.CO.[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][CH:32]=1)[CH2:7][NH:8][C:9]([C:11]1[NH:12][C:13]2[C:18]([C:19]=1[S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:21])=[O:22])=[CH:17][C:16]([Cl:29])=[CH:15][CH:14]=2)=[O:10]

Participants

6

Reactant 2

HCID 22401507HCID 22401507, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 483550HCID 483550, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3-nitrobenzyl) 3-phenylsulfonyl-5-chloroindole-2-carboxamide (353 mg, 0.75 mmol) in tetrahydrofuran (25 mL) and methanol (10 mL) containing platinum oxide (70 mg) was hydrogenated with an atmospheric pressure of hydrogen for 3 hours. The degassed solution was filtered to remove catalyst and the solvents evaporated. The residue was triturated with diethyl ether to give the product. Crystallization from acetonitrile gave analytically pure product, mp 247°-249° C.

Workup

  1. filtrationThe degassed solution was filtered
  2. customto remove catalyst
  3. customthe solvents evaporated
  4. customThe residue was triturated with diethyl ether
  5. customto give the product
  6. customCrystallization from acetonitrile
  7. customgave analytically pure product, mp 247°-249° C.

Sources & evidence

ORD record
ord-8f288a045d3e4ca68cb7588df27ce820
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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