3-(Methylthio)-4-nitrophenol → 4-Amino-3-(methylsulfanyl)phenol

HRID 1864667Notes

Reaction equation

HRID 1864667 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>C(O)(=O)C.C(O)C.[Fe]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([OH:12])=[CH:4][C:3]=1[S:2][CH3:1]

Participants

5

Reactant 1

HCID 441857023-(Methylthio)-4-nitrophenol

Product 1

HCID 190483494-Amino-3-(methylsulfanyl)phenolYield 53%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Iron powder (1.59 g, 28.5 mmol) was added slowly to a solution of 3-(methylthio)-4-nitrophenol (1.76 g, 9.5 mmol) in acetic acid (50 mL) and ethanol (5 mL). The mixture was stirred 17 hours at room temperature.v Then iron was removed with a magnet and the slurry mixture filtered. The filtrate was diluted in water (100 mL) and neutralised with a saturated solution of Na2CO3. The mixture was extracted with DCM, and the combined organic layer dried over Na2SO4. Then, the solvent was evaporated under vacuum to provide the title compound (780 mg, 53%) as a grey powder. 1H-NMR (δ, ppm, DMSO-d6): 2.29 (s, 3H, HMe), 4.48 (bs, 2H, NH2), 6.44 (d, 1H, Harom 5, J6-5=8.5 Hz), 6.54 (d, 1H, Harom 6, J6-5=8.5 Hz), 6.61 (s, 1H, Harom 2), 8.58 (broad s, 1H, OH). GC-MS (m/z): 155.09

Workup

  1. customv Then iron was removed with a magnet
  2. filtrationthe slurry mixture filtered
  3. additionThe filtrate was diluted in water (100 mL)
  4. extractionThe mixture was extracted with DCM
  5. dry with materialthe combined organic layer dried over Na2SO4
  6. customThen, the solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-5314b720e0e64eb7850df01451e2d83c
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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