Ethyl Acetate → 2-Ethyl-5-(methylsulfonyl)aniline

HRID 2390204Notes

Reaction equation

HRID 2390204 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[C:7]([N+:13]([O-])=O)[CH:6]=1)(=[O:4])=[O:3].CCOC(C)=O>CC(O)=O.[Fe]>[CH2:11]([C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][C:7]=1[NH2:13])[CH3:12]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 585219244-(Methylsulfonyl)-2-nitro-1-vinylbenzene2×

Product 1

HCID 283558962-Ethyl-5-(methylsulfonyl)aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 4-(methylsulfonyl)-2-nitro-1-vinylbenzene (Intermediate 121; 3.60 g; 15.8 mmol) in AcOH (100 mL) was treated with a solution of iron (15.9 g; 285 mmol) in AcOH (20 ml) and the reaction mixture was stirred at 60° C. for 1 h. EtOAc was added and the solution was filtered, the solvents removed under reduced pressure. The residue was taken up in EtOAc, washed with a sat. NaHCO3 solution in water, then with brine. The organic layer was dried, filtered and concentrated to give the title compound.

Workup

  1. filtrationthe solution was filtered
  2. customthe solvents removed under reduced pressure
  3. washwashed with a sat. NaHCO3 solution in water
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8799b27152d74b098446b61343b8d02b
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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