Acetophenone → 2-Phenyl-[1,6]naphthyridine-4-carboxylic acid

HRID 1822748Notes

Reaction equation

HRID 1822748 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[CH2:12][C:13](=[O:19])C(OCC)=O)=O.[OH-:22].[K+].[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)[CH3:25]>C(O)C.O>[C:27]1([C:24]2[N:5]=[C:6]3[CH:11]=[CH:10][N:9]=[CH:8][C:7]3=[C:12]([C:13]([OH:19])=[O:22])[CH:25]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 14797Potassium HydroxideHCID 54422680HCID 54422680, compound

Product 1

HCID 106821072-Phenyl-[1,6]naphthyridine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3.59 g of ethyl 4-trimethylacetamido-3-pyridylpyruvate, 2.89 g of potassium hydroxide in 10 mL of ethanol and 40 mL of water is heated at reflux for 2 hours. At this time 3.1 g of acetophenone is added and refluxing is continued for 6 hours. The ethanol is removed in vacuo, the resulting aqueous solution is washed with ether and the aqueous layer is acidified to pH5. The product is collected washed with water and dried to afford (2-phenylpyridino[4,3-b]pyridin-4-yl) carboxylic acid as a white solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. temperaturerefluxing
  4. customThe ethanol is removed in vacuo
  5. washthe resulting aqueous solution is washed with ether
  6. customThe product is collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-75a6a76cb61f46a89e1d0134458825cb
Source dataset
uspto-grants-2006_05
Patent number
US07037922B1

Reaction notes

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