4-Hydroxy-3-(4-hydroxybutyl)-1-phenyl-1,8-naphthyridin-2(1H)-one → HCID 54717824, compound

HRID 649568Notes

Reaction equation

HRID 649568 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])[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][OH:23].[CH3:24][S:25](O)(=[O:27])=[O:26].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=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:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][O:23][S:25]([CH3:24])(=[O:27])=[O:26]

Participants

3

Reactant 2

HCID 547315534-Hydroxy-3-(4-hydroxybutyl)-1-phenyl-1,8-naphthyridin-2(1H)-oneHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 54717824HCID 54717824, compound

Conditions

Temperature
55 °C

Procedure

4-Hydroxy-3-(4-hydroxybutyl)-1-phenyl-1,8- naphthyridin-2(1H)-one (10 g.) was dissolved, with stirring, in Eaton's Reagent (10% P2O5 in methanesulfonic acid; 50 ml.) under a nitrogen atmosphere. The solution was heated to 55° C. where it was held for 31/2 hr. It was then cooled and poured into a water/ice mixture. After stirring for several hours, the aqueous mixture was extracted (3x) with ethyl acetate (250 ml. each). The organic extract was separated, dried (Na2SO4), filtered and evaporated. The residue was stirred with a small volume of cold isopropanol and filtered to yield a brown solid, the mono-mesylate, which was used without further purification in Example 7.

Workup

  1. custom2 hr
  2. temperatureIt was then cooled
  3. extractionthe aqueous mixture was extracted (3x) with ethyl acetate (250 ml
  4. extractionThe organic extract
  5. customwas separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. stirringThe residue was stirred with a small volume of cold isopropanol
  10. filtrationfiltered
  11. customto yield a brown solid
  12. customthe mono-mesylate, which was used without further purification in Example 7

Sources & evidence

ORD record
ord-eeabded6c3364116b69e39e59db50432
Source dataset
uspto-grants-1988_04
Patent number
US04740511

Reaction notes

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