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

HRID 2118740Notes

Reaction equation

HRID 2118740 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 (3×) 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 (3×) 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-18e69fdd63c94250b79e2cab3816bd78
Source dataset
uspto-grants-1987_07
Patent number
US04680298

Reaction notes

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