Ammonium Hydroxide → HCID 178489909, compound

HRID 862200Notes

Reaction equation

HRID 862200 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=O)[CH:6]=[CH:7][CH:8]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH:32]=O)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C([O-])(=O)C.[NH4+:38].[OH-].[NH4+:40]>C(O)(=O)C>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[NH:38][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[N:40]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 187047601-(3-Methoxyphenyl)-2-pyridin-4-ylethane-1,2-dione

Product 1

HCID 178489909HCID 178489909, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(3-Methoxyphenyl)-2-pyridin-4-ylethane-1,2-dione (1.93 g, 8.0 mmol), 4-formylpiperidine-1-carboxylic acid tert-butyl ester (1.7 g, 8.0 mmol) and ammonium acetate (6.2 g, 80 mmol) were dissolved in acetic acid (20 mL) and heated to reflux for 2 hours, then allowed to cool to ambient temperature. The reaction mixture was poured over an ammonium hydroxide (50 mL) and ice mixture, extracted with ethyl acetate (3×125 mL) and the combined organic layers dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure. The resulting oil was chromatographed on silica gel eluting with ethyl acetate to give the imidazole as a foam (1.2 g), which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate (3×125 mL)
  4. dry with materialthe combined organic layers dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting oil was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-2f90c00743e84d3e98eb305821cda81f
Source dataset
uspto-grants-1998_02
Patent number
US05717100

Reaction notes

Loading…