HCID 10613312, compound → HCID 10729899, compound

HRID 1451097Notes

Reaction equation

HRID 1451097 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-])=O>C(O)C.[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 10613312HCID 10613312, compound

Product 1

HCID 10729899HCID 10729899, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-nitro-4-[(methylsulfonyl)amino]benzoate (1.0 g, 0.0035 mol) was dissolved in ethanol (40 mL) and hydrogenated at 20 psi in the presence of platinum oxide (Aldrich, 0.02 g) for 1 h. The catalyst was removed by filtration through Celite and the filtrate was concentrated to 20 mL. On cooling, a precipitate formed which was separated by filtration, washed with cold ethanol, and dried to give 0.75 g (84%) of ethyl 3-amino-4-[(methylsulfonyl)amino]benzoate as a white powder, mp 151° C.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated to 20 mL
  3. temperatureOn cooling
  4. customa precipitate formed which
  5. customwas separated by filtration
  6. washwashed with cold ethanol
  7. customdried

Sources & evidence

ORD record
ord-cc090785d3f04dbc9e2e074919654e6e
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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