HCID 20583266, compound → HCID 85803722, compound

HRID 411219Notes

Reaction equation

HRID 411219 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([S:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:10])=[O:9])[CH:7]=1.[H][H]>CO.[Pd]>[NH2:16][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][C:6]=1[S:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 20583266HCID 20583266, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 85803722HCID 85803722, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium (10%) on carbon is added to a solution of methyl ((5-methyl-2-nitro-phenyl)sulfonyl)acetate (Preparation 37, 2.0 g) in MeOH (60 mL) and the solution is shaken on a Parr apparatus under 30 psi of hydrogen. After 3 hours the solution is filtered through Celite and the filter cake eluted with MeOH (60 mL). The combined MeOH eluant is evaporated and the remaining residue placed under high vacuum overnight to obtain 1.76 g (99%) of the title compound as a dark solid. Physical characteristics: MS (ESI+) m/z 244 (M+H).

Workup

  1. filtrationAfter 3 hours the solution is filtered through Celite
  2. washthe filter cake eluted with MeOH (60 mL)
  3. customThe combined MeOH eluant is evaporated
  4. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-c37dd00edc08404685046128b31fa557
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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