5-Phenyl-2-pyridinamine → HCID 44594744, compound

HRID 1520430Notes

Reaction equation

HRID 1520430 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH2:21][C:22](OCC)=[O:23])=[CH:16][CH:15]=1.C([O-])(=O)C.[NH4+]>O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([CH:12]=2)[C:22](=[O:23])[CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=2)[N:13]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1050975-Phenyl-2-pyridinamineHCID 517165Ammonium AcetateHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

Product 1

HCID 44594744HCID 44594744, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 0.20 g (1.17 mmol) of 5-phenylpyridin-2-amine and 0.227 g (1.17 mmol) of ethyl 3-(4-pyridinyl)-3-oxopropionate were added 0.180 g (2.34 mmol) of ammonium acetate. The reaction mixture was heated at 140° C. for 12 hours. After cooling, water was added and the mixture was extracted with chloroform. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and evaporated. The resulting solid was dissolved in methanol and purified on preparative thin layer chromatography eluting with a mixture of ethylacetate/ethanol in the proportions 95/5 to afford 0.10 g (28%) of the desired compound which was transformed into the oxalate salt in the usual manner to give the pure product as a solid.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. dissolutionThe resulting solid was dissolved in methanol
  7. custompurified on preparative thin layer chromatography
  8. washeluting with a mixture of ethylacetate/ethanol in the proportions 95/5

Sources & evidence

ORD record
ord-81b53b7ba5af49dc8becf27f72e23fbb
Source dataset
uspto-grants-2015_07
Patent number
US09073915B2

Reaction notes

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