Pyridine → HCID 86751067, compound

HRID 1939324Notes

Reaction equation

HRID 1939324 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH:16]=[CH:15][N:14]=[C:13]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:8][CH:7]=2)=O)[CH2:3][CH2:2]1.[ClH:23].Cl.NCC[NH:28][OH:29].[N:30]1C=CC=[CH:32][CH:31]=1>C(O)C>[ClH:23].[ClH:23].[NH2:30][CH2:31][CH2:32][O:29][N:28]=[C:4]([CH:1]1[CH2:3][CH2:2]1)[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 19078333HCID 19078333, compoundHCID 86751068HCID 86751068, compound

Product 1

HCID 86751067HCID 86751067, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cyclopropyl-[4-(2-phenyl-1-imidazolyl)phenyl]methanone (2.6 g), aminoethylhydroxylamine dihydrochloride (1.95 g), and 3 equivalents of pyridine, in absolute ethanol (30 ml) was heated under reflux, under nitrogen, with stirring, overnight. The reaction mixture was evaporated, the residue was taken up in ethyl acetate and washed with a 10% sodium hydroxide solution. The organic extracts were evaporated and the residue purified by high performance liquid chromatography (silica gel, 185:14:1 dichloromethane/methanol/ammonium hydroxide). The appropriate fractions were collected and concentrated. The residue was taken up in ethanol and treated with ethereal hydrogen chloride. The mixture was evaporated. The residue was recrystallized from ethanol/ether to give 3.06 g (80.9%) of product, mp>220° C. (dec).

Workup

  1. temperatureunder reflux, under nitrogen
  2. customThe reaction mixture was evaporated
  3. washwashed with a 10% sodium hydroxide solution
  4. customThe organic extracts were evaporated
  5. customthe residue purified by high performance liquid chromatography (silica gel, 185:14:1 dichloromethane/methanol/ammonium hydroxide)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated
  8. additiontreated with ethereal hydrogen chloride
  9. customThe mixture was evaporated
  10. customThe residue was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-026848debf6a48ed9253bc9e743ebd4e
Source dataset
uspto-grants-1997_12
Patent number
US05696142

Reaction notes

Loading…