Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylate → Methyl 3-amino-4-(methylthio)benzoate

HRID 356918Notes

Reaction equation

HRID 356918 reaction equation
[CH3:1][S:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-])=O>CO.[Pd]>[NH2:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[S:2][CH3:1])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 21187831Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylate

Product 1

HCID 21187837Methyl 3-amino-4-(methylthio)benzoateYield 59.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred solution of methyl 4-methylthio-3-nitrobenzoate (6.82 g) in methanol (350 mL) is hydrogenated using a 5% w/w palladium on charcoal catalyst (0.8 g) at room temperature for 48 hours. After filtration the solution is concentrated, to give methyl 3-amino-4-(methylthio)benzoate (3.5 g), in the form of a pale yellow solid m.p. 63°-65° C.

Workup

  1. customat room temperature
  2. customfor 48 hours
  3. filtrationAfter filtration the solution
  4. concentrationis concentrated

Sources & evidence

ORD record
ord-007da07fd5e846f0b02cc8dbbb8aba9c
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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