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

HRID 605167Notes

Reaction equation

HRID 605167 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 136A, 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 under vacuum 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 under vacuum

Sources & evidence

ORD record
ord-4a25c8226a654b51b38d63a38d6243fc
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…