HCID 178478844, compound → HCID 69904327, compound

HRID 357620Notes

Reaction equation

HRID 357620 reaction equation
[ClH:1].Cl.O[NH:4][C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[N:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[NH2:22])=[NH:6]>[Ni].CO.O>[ClH:1].[ClH:1].[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[N:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[NH2:22])(=[NH:4])[NH2:6]

Participants

4

Reactant 1

HCID 178478844HCID 178478844, compound

Product 1

HCID 69904327HCID 69904327, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

0.3 g of Raney nickel is added to a solution of 0.8 g (2.33 mmol) of 1-[4-(N-hydroxy-amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-imidazole dihydrochloride in 60 ml of methanol/water (1:1), and hydrogenation is carried out at room temperature and under normal pressure until the absorption of hydrogen has ceased. The filtrate is adjusted to pH 3 with a small amount of 3N methanolic hydrochloric acid and is concentrated by evaporation in vacuo. Recrystallization of the residue from methanol/water yields the title compound, m.p. >260° C., 1H-NMR (D2O): δ=8.15 (d, 1H); 7.82 (d, 1H); 7.58 (t, 1H); 7.17 (d, 1H); 6.90 (d, 1H); 3.29-3.35 (m, 2H); 3.12-3.18 (m, 2H).

Workup

  1. customis carried out at room temperature and under normal pressure until the absorption of hydrogen
  2. concentrationis concentrated by evaporation in vacuo
  3. customRecrystallization of the residue from methanol/water

Sources & evidence

ORD record
ord-243d2fa0c9db49fc8737aa44c647ba59
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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