2-Aminopyridine → HCID 44594742, compound

HRID 1520429Notes

Reaction equation

HRID 1520429 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[N:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][C:16](OCC)=[O:17])=[CH:10][CH:9]=1.[OH-].[Na+]>O>[N:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:7]=[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]3[C:16](=[O:17])[CH:15]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 14798Sodium HydroxideHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

Product 1

HCID 44594742HCID 44594742, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

0.406 g (4.31 mmol) of pyridin-2-amine and 1.00 g (5.17 mmol) of ethyl 3-(4-pyridinyl)-3-oxopropionate were added to 3 g of polyphosphoric acid (84% min.). The reaction mixture was heated at 140° C. for 12 hours. After cooling, water was added and the mixture was neutralized with an aqueous solution of sodium hydroxide (30%) and extracted with chloroform. The extracts were washed with a saturated aqueous solution of sodium chloride, dried and evaporated. The residue obtained was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 99/1/0.1 to 85/15/1.5 to give 0.154 g (16%) 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. extractionextracted with chloroform
  3. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 99/1/0.1 to 85/15/1.5

Sources & evidence

ORD record
ord-4041bf8dbbea4125a7ae3a69eeea8b06
Source dataset
uspto-grants-2015_07
Patent number
US09073915B2

Reaction notes

Loading…