Ammonium Chloride → HCID 19605493, compound

HRID 1603631Notes

Reaction equation

HRID 1603631 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:3]=1.[NH4+].[Cl-]>CO.O1CCOCC1.O.[Fe]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([C:4]2[CH:3]=[C:2]([Br:1])[N:7]=[C:6]([C:8]#[N:9])[CH:5]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 19605504HCID 19605504, compound

Product 1

HCID 19605493HCID 19605493, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 21966525Dioxane MethanolSolvent

Procedure

0.184 g (0.0005 mol) of 6-bromo-4-(4-nitrobenzenesulphonyl)-pyridine-2-carbonitrile was dissolved in 10 ml of methanol/dioxane, treated with 0.37 g of iron powder and a solution of 0.37 g of NH4Cl in 10 ml of water and boiled at reflux for 2 hrs. Then, the reaction mixture was filtered and the filter cake was rinsed with methanol and ethyl acetate. The filtrate was concentrated and the residue was dissolved in ethyl acetate, washed with sat. NaHCO3 solution, water and sat. sodium chloride solution, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:4. There was obtained 0.13 g (75%) of 4-(4-aminobenzenesulphonyl)-6-bromopyridine-2-carbonitrile as yellow crystals; m.p.: 186-188° C.

Workup

  1. temperatureat reflux for 2 hrs
  2. filtrationThen, the reaction mixture was filtered
  3. washthe filter cake was rinsed with methanol and ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with sat. NaHCO3 solution, water and sat. sodium chloride solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:4

Sources & evidence

ORD record
ord-4a2e5ade45414e16b85963dd0735c3bd
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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