Acetic Acid → Benzoic acid, 5-amino-2-(methylthio)-, methyl ester

HRID 2230581Notes

Reaction equation

HRID 2230581 reaction equation
[CH3:1][S:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(O)(=O)C.O>[Fe].C(OCC)(=O)C.CCCCCC>[CH3:1][S:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 7164673Methyl 2-(methylsulfanyl)-5-nitrobenzoate

Product 1

HCID 18465011Benzoic acid, 5-amino-2-(methylthio)-, methyl ester

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
90 °C

Procedure

Combine methyl 2-methylthio-5-nitrobenzoate (2.9 g, 12.7 mmol) and glacial acetic acid (100 mL). Heat to 90° C. Add iron powder (5 g) and water (20 mL) over about 10 minutes. After 30 minutes, the reaction mixture was filtered while still hot and diluted with water (500 mL). Extract the reaction mixture with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 20% ethyl acetate/hexane to give methyl 2-methylthio-5-aminobenzoate. Rf=0.51 (silica gel, 30% ethyl acetate/hexane).

Workup

  1. filtrationthe reaction mixture was filtered while still hot and
  2. additiondiluted with water (500 mL)
  3. extractionExtract the reaction mixture with ethyl acetate
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-839ab7af21ba4658a3ff3fd961a1b4f7
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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