HCID 178526407, compound → HCID 469420, compound

HRID 263869Notes

Reaction equation

HRID 263869 reaction equation
[CH:1]1[C:6]([I:7])=[C:5]([N+:8]([O-])=O)[CH:4]=[C:3]2[N:11]=[C:12]([Cl:14])[NH:13][C:2]=12>CCO.[Ni]>[CH:1]1[C:6]([I:7])=[C:5]([NH2:8])[CH:4]=[C:3]2[N:11]=[C:12]([Cl:14])[NH:13][C:2]=12

Participants

4

Reactant 1

HCID 178526407HCID 178526407, compound

Product 1

HCID 469420HCID 469420, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.339 g (1.048 mmol) of 26 and 0.090 g (wet) of Ra-Ni in 10 mL of EtOH was hydrogenated at room temperature, 50 psi of H2 for 7 h. The reaction mixture was filtered and the filtrate was evaporated. The residue was chromatographed on a silica column (2×6 cm, eluted successively with 1%, 2%, 3% MeOH/CHCl3). Evaporation of fractions 11-17 (20 mL per fraction) gave 0.190 g (62%) of 26a as a foam. An analytical sample (a yellowish crystalline compound) was obtained by recrystallization from MeOH. MP: >200° C. (dec). MS: (EI) m/e 292.9202 (100%, M+ =292.9217). 1H NMR (DMSO-d6): d 12.80 (br s, 1, 1-NH), 7.75 (s, 1, 4-H), 6.87 (s, 1, 7-H), 5.03 (s, 2, 6-NH2). Anal. Calcd. for C7H5ClIN3 : C, 28.65; H, 1.72; N, 14.32. Found: C, 28.84; H, 1.66; N, 14.17.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was chromatographed on a silica column (2×6 cm
  5. washeluted successively with 1%, 2%, 3% MeOH/CHCl3)
  6. customEvaporation of fractions 11-17 (20 mL per fraction)

Sources & evidence

ORD record
ord-a2443dc93ee846289dae91939794eac4
Source dataset
uspto-grants-1997_07
Patent number
US05646125

Reaction notes

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