HCID 10689660, compound → HCID 19353518, compound

HRID 610836Notes

Reaction equation

HRID 610836 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14](Br)[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][N:15]=[C:16]([NH:18][CH3:19])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10689660HCID 10689660, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19353518HCID 19353518, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.5 g (0.0014 mol) of 4-amino-N-(2-bromo-6-methylamino-pyridin-4-yl)-benzenesulfonamide was dissolved in 25 ml of ethanol, treated with 0.05 g of Pd/C and hydrogenated with hydrogen gas under normal pressure for 1 hour. The catalyst was filtered off, the filtrate was concentrated and the residue was dissolved in 10 ml of 1N NaOH, filtered and the filtrate was then adjusted pH 8 by means of 1N HCl. The precipitate which separated slowly was filtered off under suction, rinsed and dried in a high vacuum. There was obtained 0.22 g (57%) of 4-amino-N-(2-methylamino-pyridin-4-yl)-benzenesulfonamide as white crystals; m.p.: >261° C. (dec).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionthe residue was dissolved in 10 ml of 1N NaOH
  4. filtrationfiltered
  5. customThe precipitate which separated slowly
  6. filtrationwas filtered off under suction
  7. washrinsed
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-c1f66338617f48ae8b5611d2d4295fa5
Source dataset
uspto-grants-1999_12
Patent number
US05998665

Reaction notes

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