Ammonium Chloride → HCID 136166859, compound

HRID 1617440Notes

Reaction equation

HRID 1617440 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=O)=[CH:5][CH:4]=1.Cl.[NH2:27][OH:28].C(=O)([O-])O.[Na+].[NH4+].[Cl-]>C(O)C.O.CCOC(C)=O>[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10]/[C:11](/[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:27]\[OH:28])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66668687HCID 66668687, compound

Product 1

HCID 136166859HCID 136166859, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

A solution of 3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one (838 mg), hydroxylamine hydrochloride (353 mg) and sodium hydrogencarbonate (426 mg) in ethanol/water (21 mL, 20:1) was heated under reflux for 2 hours. A saturated aqueous solution of NH4Cl was added to the reaction mixture and extraction was made with EtOAc (2×). The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Column chromatography on silica gel (EtOAc/n-heptane 2:1) gave (E)-3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (420 mg, 48%) as a white foam, MS (ESI+): m/z=346.1 ([M+H]+), (Z)-3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (20 mg, 2%) as a colorless oil, MS (ESI+): m/z=346.1 ([M+H]+) and 3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime as a mixture of isomers (313 mg, 36%), MS (ESI+): m/z=346.1 ([M+H]+).

Workup

  1. temperatureunder reflux for 2 hours
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf4435c3c9794a068d82ba0599de3b7c
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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