Ethyl Acetate → HCID 19605507, compound

HRID 1603605Notes

Reaction equation

HRID 1603605 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([CH3:20])[N:3]=1.[NH4+].[Cl-].C(OCC)(=O)C>CO.O.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH:5]=[C:4]([CH3:20])[N:3]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19605450HCID 19605450, compound

Product 1

HCID 19605507HCID 19605507, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

0.15 g (0.00042 mol) of 2-bromo-6-methyl-4-(4-nitrobenzenesulphonyl)-pyridine was dissolved in 10 ml of methanol, treated with 0.18 g of iron powder and a solution of 0.18 g of NH4Cl in 5 ml of water and heated at reflux for 1 hr. 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 dried in a high vacuum. There was obtained 0.134 g (98%) of 4-(2-bromo-6-methylpyridine-4-sulphonyl)-phenylamine as yellowish crystals; m.p.: 189-191° C.

Workup

  1. temperatureat reflux for 1 hr
  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 dried in a high vacuum

Sources & evidence

ORD record
ord-a9e63e2547b542459b6462ea494422ac
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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