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

HRID 1862596Notes

Reaction equation

HRID 1862596 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-3589798437004ad794164a3b8670f7d4
Source dataset
uspto-grants-2003_03
Patent number
US06538150B2

Reaction notes

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