Hydrochloric Acid → Methyl 2-amino-4-{[(methylsulfonyl)amino]methyl}benzoate

HRID 458133Notes

Reaction equation

HRID 458133 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([N+:17]([O-])=O)[CH:8]=1)(=[O:4])=[O:3].Cl.[H][H]>CO.[Pd]>[NH2:17][C:9]1[CH:8]=[C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22494948HCID 22494948, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11288376Methyl 2-amino-4-{[(methylsulfonyl)amino]methyl}benzoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

13.25 g (46 mmol) of methyl 4-methanesulfonylaminomethyl-2-nitrobenzoate are dissolved in 200 ml of methanol. After addition of 1.4 ml (46 mmol) of concentrated hydrochloric acid and 1 g of Pd catalyst (10% on active charcoal), the mixture is hydrogenated with hydrogen under atmospheric pressure until the hydrogen uptake is complete. The mixture is removed from the catalyst by filtration and the filtrate is concentrated completely. Crystallization of the residue from water yields 10.4 g (88%) of methyl 2-amino-4-methanesulfonylaminomethylbenzoate of melting point 121–122° C.

Workup

  1. customThe mixture is removed from the catalyst by filtration
  2. concentrationthe filtrate is concentrated completely
  3. customCrystallization of the residue from water

Sources & evidence

ORD record
ord-d428dcd4e0cc49ccb3ef14c8f8eb218f
Source dataset
uspto-grants-2007_03
Patent number
US07189848B2

Reaction notes

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