Methanesulfonic Acid → HCID 13176884, compound

HRID 371425Notes

Reaction equation

HRID 371425 reaction equation
CS(O)(=O)=O.[N+:6]([C:9]1[CH:30]=[CH:29][C:12]([C:13]([O:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:26](=[NH:28])[NH2:27])[CH:22]=3)[CH:17]=2)=[O:14])=[CH:11][CH:10]=1)([O-])=O.CS(O)(=O)=O>[Pd].CN(C=O)C>[NH2:6][C:9]1[CH:30]=[CH:29][C:12]([C:13]([O:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:26](=[NH:27])[NH2:28])[CH:22]=3)[CH:17]=2)=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 13176881HCID 13176881, compound

Product 1

HCID 13176884HCID 13176884, compoundYield 164.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.0 g of 6-amidino-2-naphthyl 4-nitrobenzoate methanesulfonate, 0.88 g of methanesulfonic acid, 0.3 g of 10% Pd-C and anhydrous DMF was subjected to catalytic hydrogenation. After absorption of a stoichiometric quantity of hydrogen, the reaction mixture was freed from Pd-C by filtration. After adding ethylether to the filtrate with stirring, the precipitate was collected by filtration and recrystallized from a DMF-ethylether mixture to obtain 3.5 g of a white powder of 6-amidino-2-naphthyl 4-aminobenzoate dimethanesulfonate.

Workup

  1. customAfter absorption of a stoichiometric quantity of hydrogen
  2. filtrationthe reaction mixture was freed from Pd-C by filtration
  3. additionAfter adding ethylether to the filtrate
  4. filtrationthe precipitate was collected by filtration
  5. customrecrystallized from a DMF-ethylether mixture

Sources & evidence

ORD record
ord-983be8e85c2243c4b36ed124c29d408f
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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