Acetic Acid → HCID 23057683, compound

HRID 653896Notes

Reaction equation

HRID 653896 reaction equation
[N+](C1C=CC=CC=1C1C=CC(C[N:17]2[C:21]([CH2:22][O:23][CH3:24])=[C:20]([Cl:25])[N:19]=[C:18]2[CH2:26][CH2:27][CH2:28][CH3:29])=CC=1)([O-])=O.C(O)(=O)C>[Fe].CO>[CH2:26]([C:18]1[NH:17][C:21]([CH2:22][O:23][CH3:24])=[C:20]([Cl:25])[N:19]=1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 15698096HCID 15698096, compound

Product 1

HCID 23057683HCID 23057683, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.40 g of 1-[(2'-nitrobiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-methoxymethylimidazole, 2.10 g of iron powder, 4.25 mL of glacial acetic acid, and 200 mL of methanol was refluxed for 5 hours. After cooling, the solvent was removed in vacuo, and the residue was dissolved in ethyl acetate. The precipitated iron salts were removed by filtration through Celite®, and the resulting solution was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. Column chromatography on silica gel (elution: 10-30% ethyl acetate/benzene) furnished 2.95 g of 1-[2'-aminobiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-methoxymethylimidazole; NMR (200 MHz, CDCl3); δ 7.43 (d, 2H); 7.19-7.04 (m, 4H); 6.80 (m, 2H); 5.19 (s, 2H); 4.33 (s, 2H); 3.70 (br s, 1H); 3.28 (s, 3H); 2.59 (t, 2H); 1.67 (quint., 2H); 1.34 (sext., 2H); 0.87 (t, 3H).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customThe precipitated iron salts were removed by filtration through Celite®
  5. washthe resulting solution was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8f1148beac54413696fc8c6d0b4f4c48
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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