Methyl 5-[4-(ethylsulfonyl)phenoxy]-2-nitrobenzoate → Methyl 2-amino-5-[4-(ethylsulfonyl)phenoxy]benzoate

HRID 2080669Notes

Reaction equation

HRID 2080669 reaction equation
[CH2:1]([S:3]([C:6]1[CH:25]=[CH:24][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]([N+:21]([O-])=O)=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[H][H]>[Ni].CO>[NH2:21][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:9]2[CH:24]=[CH:25][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:7][CH:8]=2)=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 2

HCID 57433573Methyl 5-[4-(ethylsulfonyl)phenoxy]-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 57433574Methyl 2-amino-5-[4-(ethylsulfonyl)phenoxy]benzoateYield 41.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

0.7 g of Raney nickel was added to a methanol (150 ml) solution of 6.98 g of methyl 5-[4-(ethylsulfonyl)phenoxy]-2-nitrobenzoate, and stirred overnight in a hydrogen atmosphere. The catalyst was removed through filtration, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1) to obtain 2.65 g of the entitled compound as a colorless oil.

Workup

  1. customThe catalyst was removed through filtration
  2. customthe solvent was evaporated away under reduced pressure
  3. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-105941c73559491bac8c38c208e349f1
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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