Ammonium Acetate → HCID 70165645, compound

HRID 2228610Notes

Reaction equation

HRID 2228610 reaction equation
Cl.[NH2:2][CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4](=O)[CH3:5].[C:13]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH2:25]([O:24][C:22]([C:21]1[C:4]([CH3:5])=[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:2][C:13]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 27970031-amino-1-phenylpropan-2-one hydrochloride

Product 1

HCID 70165645HCID 70165645, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-amino-1-phenyl-propan-2-on hydrochloride (10.5 g, 50.5 mmol), ethyl isonicotinoylacetate (8.1 g, 42.1 mmol), and ammonium acetate (6.5 g, 84.2 mmol) in acetic acid (50 mL) was heated under reflux temperature for 6 hours. After cooling, the mixture was diluted with ice-water (50 mL). The whole was extracted with CH2Cl2 (30 mL×3), and the combined organic layers were dried over MgSO4, and concentrated in vaciio. The residue was purified by flash chromatography eluting with hexane-ethyl acetate (2 : 1) to afford the title product (2.1 g, 16% yield) as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux temperature for 6 hours
  3. temperatureAfter cooling
  4. extractionThe whole was extracted with CH2Cl2 (30 mL×3)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vaciio
  7. customThe residue was purified by flash chromatography
  8. washeluting with hexane-ethyl acetate (2 : 1)

Sources & evidence

ORD record
ord-87f9acb6031849e3be5deddfbb1c9205
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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