HCID 66643213, compound → HCID 66642739, compound

HRID 869231Notes

Reaction equation

HRID 869231 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N+:14]([O-])=O)(=[O:6])=[O:5])([CH3:3])[CH3:2]>[Fe].C(O)(=O)C>[CH:1]([S:4]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[NH2:14])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66643213HCID 66643213, compound

Product 1

HCID 66642739HCID 66642739, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-(isopropylsulfonyl)-4-methyl-1-nitrobenzene (Preparation Example 291) (7.41 g) and acetic acid (70 mL), iron powder (5.43 g) was added and stirred at 80° C. for 3 hours. Thereafter, insoluble materials in the reaction liquid were removed, and the solvent was distilled off under reduced pressure. After addition of ethyl acetate (150 mL) and removal of insoluble materials, the residue was washed with water and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was washed with ethyl acetate-diisopropyl ether to give 2-(isopropylsulfonyl)-4-methylaniline (3.86 g) as a light yellow solid.

Workup

  1. additionwas added
  2. customThereafter, insoluble materials in the reaction liquid
  3. customwere removed
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionAfter addition of ethyl acetate (150 mL) and removal of insoluble materials
  6. washthe residue was washed with water and saturated aqueous sodium chloride
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. washThe residue was washed with ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-5de6904a48e04e0eb3ff5ed4bc8b8a5d
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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