Water → HCID 22038820, compound

HRID 1016746Notes

Reaction equation

HRID 1016746 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([NH:15][C:16]1[CH:21]=[CH:20][C:19](/[C:22](=[N:25]/[H])/[NH:23]O)=[CH:18][CH:17]=1)[C:12]([OH:14])=[O:13].O>C(O)(=O)C.[Ni]>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][CH:11]([C:4]2[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:12]([OH:14])=[O:13])=[CH:21][CH:20]=1)(=[NH:23])[NH2:25]

Participants

5

Reactant 2

HCID 962WaterHCID 178506507HCID 178506507, compound

Product 1

HCID 22038820HCID 22038820, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent2×

Procedure

555 mg of (Z)-(RS)-(2,5-dimethoxy-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid were stirred under hydrogen in 8 ml of acetic acid and 16 ml of water in the presence of Raney-nickel. After the addition 13 ml of acetic acid the solution was filtered clear and evaporated in a vacuum. The residue was triturated in water and then in methanol, filtered off under suction and dried. There were obtained 404 mg of (RS)-(4-carbamimidoyl-phenylamino)-(2,5-dimethoxy-phenyl)-acetic acid, m.p. 310° C., MS: 330 (M+H)+.

Workup

  1. filtrationwas filtered clear
  2. customevaporated in a vacuum
  3. customThe residue was triturated in water
  4. filtrationin methanol, filtered off under suction
  5. customdried

Sources & evidence

ORD record
ord-198fc77b82b342a7b196f267acfbaa4c
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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