Ethyl Acetate → HCID 19605473, compound

HRID 1603603Notes

Reaction equation

HRID 1603603 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[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])[N:3]=1.[NH4+].[Cl-].C(OCC)(=O)C>CO.O1CCOCC1.O.[Fe]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([C:4]2[CH:5]=[C:6]([NH:8][CH3:9])[CH:7]=[C:2]([Br:1])[N:3]=2)(=[O:11])=[O:12])=[CH:14][CH:15]=1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19605444HCID 19605444, compound

Product 1

HCID 19605473HCID 19605473, compoundYield 88%

Reagents, catalysts & solvents 4

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

Procedure

0.078 g (0.00021 mol) of [2-bromo-6-(4-nitrobenzenesulphonyl) -pyridin-4-yl]-methylamine was dissolved in a mixture of 1.5 ml of methanol and 1.5 ml of dioxane, treated with 0.078 g of iron powder and a solution of 0.078 g of NH4Cl in 2.5 ml of water and heated at reflux for 2 hrs. Therafter, 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 silical gel with ethyl acetate/hexane 1:3. There was obtained 0.063 g (88%) of [2-(4-aminobenzenesulphonyl)-6-bromopyridin-4-yl]-methylamine as yellowish crystals; m.p.: 158-160° 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 silical gel with ethyl acetate/hexane 1:3

Sources & evidence

ORD record
ord-e14a0a2544fe475fa759e025b6ae2a34
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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