Ethyl Acetate → HCID 19605463, compound

HRID 1603601Notes

Reaction equation

HRID 1603601 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:3]=1.[NH4+].[Cl-].C(OCC)(=O)C>CO.O1CCOCC1.O.[Fe]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([C:4]2[CH:5]=[C:6]([NH2:8])[CH:7]=[C:2]([Br:1])[N:3]=2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19605527HCID 19605527, compound

Product 1

HCID 19605463HCID 19605463, compoundYield 44%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.10 g (0.00026 mol) of 2-bromo-4-nitro-6-(4-nitrobenzenesulphonyl)-pyridine was dissolved in a mixture of 1.5 ml of methanol and 1.5 ml of dioxane, treated with 0.20 g of iron powder and a solution of 0.20 g of NH4Cl in 2.5 ml of water and heated at reflux for 2 hrs. Thereafter, the reaction mixture was poured into a mixture of ethyl acetate and water, suction filtered and the organic phase was extracted with water and sat. sodium chloride solution and dried over MgSO4. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:4. There was obtained 0.037 g (44%) of 2-(4-aminobenzenesulphonyl)-6-bromopyridin-4-ylamine as yellowish crystals; m.p.: 202-204° C.

Workup

  1. temperatureat reflux for 2 hrs
  2. filtrationfiltered
  3. extractionthe organic phase was extracted with water and sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate/hexane 1:4

Sources & evidence

ORD record
ord-8552d7920ca94c86a19181d44d53ac19
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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