Water → HCID 23223373, compound

HRID 399874Notes

Reaction equation

HRID 399874 reaction equation
C([O:8][C:9]([C:11]1[N:12]([C:16]2[CH:17]=[C:18]([CH:25]=[CH:26][CH:27]=2)[C:19]([N:21]=[C:22]([NH2:24])[NH2:23])=[O:20])[CH:13]=[CH:14][CH:15]=1)=[O:10])C1C=CC=CC=1.O.C(=O)([O-])[O-].[K+].[K+]>CO.[C].[Pd]>[C:9]([C:11]1[N:12]([C:16]2[CH:17]=[C:18]([CH:25]=[CH:26][CH:27]=2)[C:19]([N:21]=[C:22]([NH2:23])[NH2:24])=[O:20])[CH:13]=[CH:14][CH:15]=1)([OH:10])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 18945195HCID 18945195, compound

Product 1

HCID 23223373HCID 23223373, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon (0.2 g) was added to a mixture of 2-[3-(2-benzyloxycarbonylpyrrol-1-yl)benzoyl]guanidine (1.2 g) in methanol and the mixture was hydrogenated at ambient temperature under an atmospheric pressure. After the mixture was added to water, and the mixture was adjusted to pH 10 with potassium carbonate. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was dissolved in a mixture of water and ethyl acetate and the separated aqueous layer was adjusted to pH 5 with 6N-hydrochloric acid. The isolated precipitate was collected by filtration and the precipitate was recrystallized from a mixture of methanol, dioxane and diisopropyl ether to give 2-[3-(2-carboxypyrrol-1-yl) benzoyl]guanidine (0.41 g).

Workup

  1. customwas hydrogenated at ambient temperature under an atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of water and ethyl acetate
  5. filtrationThe isolated precipitate was collected by filtration
  6. customthe precipitate was recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-a489d5fcd09d495f99a94de03b7c5578
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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