3-(Pyridin-4-yl)propanoic acid → HCID 54676197, compound

HRID 1822188Notes

Reaction equation

HRID 1822188 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](O)=[O:28])=[CH:21][CH:20]=1>O>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:4](=[O:18])[C:3]=1[C:27](=[O:28])[CH2:26][CH2:25][C:22]1[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 2332433-(Pyridin-4-yl)propanoic acidHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 54676197HCID 54676197, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-hydroxy-1-phenyl-1,8-naphthyridin-2 (1H)-one (2.0 g, 8.4 mmol; synthesized according to JP, A, 61-246183 (1986)), 3-(pyridin-4-yl)propionic acid (19.03 g, 126 mmol, 15 eq.) and polyphosphoric acid (about 100 ml) was heated overnight at 150° C. while stirring. The mixture was poured into water with stirring to form a solution while it was occasionally cooled. The operation including 3 times washing of the aqueous layer with chloroform, then addition of saturated aqueous sodium hydrogen carbonate followed by occasional extraction with chloroform was repeated until the aqueous layer was made pH3 to 3.5. The organic layers which were collected during neutralizing were pooled, dried over anhydrous magnesium sulfate, and then evaporated to give a residue which was purified by flash column chromatography to afford 4-hydroxy-3-[1-oxo-3-(pyridin-4-yl)propyl]-1-phenyl-1,8-naphthyridin-2 (1H)-one (1.59 g, 51%) as crystals.

Workup

  1. stirringwith stirring
  2. customto form a solution while it
  3. temperaturewas occasionally cooled
  4. washwashing of the aqueous layer with chloroform
  5. additionaddition of saturated aqueous sodium hydrogen carbonate
  6. extractionfollowed by occasional extraction with chloroform
  7. customThe organic layers which were collected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customto give a residue which
  11. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-bca98e6449964ac6b1e2d9328b71f805
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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