HCID 67516104, compound → HCID 67516005, compound

HRID 2173399Notes

Reaction equation

HRID 2173399 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[CH2:12][C:13]([OH:15])=[O:14]>O.N.O>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([CH2:12][C:13]([OH:15])=[O:14])=[C:3]([S:2][CH3:1])[CH:8]=1

Participants

4

Reactant 1

HCID 67516104HCID 67516104, compound

Product 1

HCID 67516005HCID 67516005, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 12896473Azane;hydrateSolvent2×

Procedure

A solution of [2-(methylsulfanyl)-4-nitrophenyl]acetic acid (230 mg, 1.0 mmol) in 10 mL of water and 0.6 mL of NH3.H2O was added a solution of FeSO4.7H2O (2.25 g, 8.1 mmol) in 10 mL of water and another 1.6 mL of NH3.H2O were added dropwise. The mixture was stirred at 60˜80° C. overnight. The mixture was filtered and the filtrate was acidified to pH 4˜5 with HOAc. Extracted with EtOAc and the combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to afford [4-amino-2-(methylsulfanyl)phenyl]acetic acid.

Workup

  1. filtrationThe mixture was filtered
  2. extractionExtracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-114f04229203459f901dba315d490823
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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