Methanol → 3-Amino-4-(4-methoxy-phenylsulfanyl)-benzoic acid methyl ester

HRID 883866Notes

Reaction equation

HRID 883866 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:6]([N+:19]([O-])=O)[CH:5]=1.[Cl-].[NH4+].CO.O1CCCC1>[Fe].O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:6]([NH2:19])[CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 41664294-(4-Methoxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

Product 1

HCID 613055833-Amino-4-(4-methoxy-phenylsulfanyl)-benzoic acid methyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a solution of the product from Example 13A, iron powder and ammonium chloride in a methanol, tetrahydrofuran, and water solution was heated to reflux. The resultant mixture was filtered, and the filtrate was concentrated. Then ethyl acetate was added, stirred, filtered and concentrated to provide the title compound (7.16 g, 90%).

Workup

  1. filtrationThe resultant mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThen ethyl acetate was added
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b1f4d3b3ab3c4c358ded46292581f8db
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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