Ammonium Chloride → 3-Amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester

HRID 605349Notes

Reaction equation

HRID 605349 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[C:6]([N+:18]([O-])=O)[CH:5]=1.[NH4+].[Cl-]>CCO.CCOC(C)=O.[Fe]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[C:6]([NH2:18])[CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 668084784-(4-Hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

Product 1

HCID 668086283-Amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester (5.60 g, 18 mmol), Fe powder (5.34 g, 92 mmol) and NH4Cl (4.91 g, 92 mmol) in aqueous EtOH [prepared from EtOH (50 mL) and H2O (50 mL)] was gradually heated to reflux and refluxed for 45 minutes. The reaction mixture was diluted with AcOEt (50 mL) and filtered through celite pad. The filtrate was evaporated and the aqueous residue was portioned between AcOEt and 10% NaHCO3. The organic layer was separated, washed with H2O and brine, dried over MgSO4 and evaporated to give pale yellow solid. The resulting solid was washed with i-Pr2O and dried at 40° C. for 3 days under reduced pressure to give the title compound as slightly yellow crystal (4.50 g, 90% by 2 steps).

Workup

  1. temperaturewas gradually heated
  2. temperatureto reflux
  3. temperaturerefluxed for 45 minutes
  4. filtrationfiltered through celite pad
  5. customThe filtrate was evaporated
  6. customThe organic layer was separated
  7. washwashed with H2O and brine
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customto give pale yellow solid
  11. washThe resulting solid was washed with i-Pr2O
  12. customdried at 40° C. for 3 days under reduced pressure

Sources & evidence

ORD record
ord-5cea0750b472475c83da2014d7820e62
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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