Sodium Hydroxide → 1,2,3,4-Tetrahydro-1,8-naphthyridin-4-one

HRID 2118687Notes

Reaction equation

HRID 2118687 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5](C2C=CC=CC=2)[C:4](=O)[C:3]=1CCO.[OH-].[Na+]>S(=O)(=O)(O)O>[NH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][N:7]=2)[C:2](=[O:1])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 547236674-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 198908801,2,3,4-Tetrahydro-1,8-naphthyridin-4-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-hydroxy-3-(2-hydroxyethyl)1-phenyl-1,8-naphthyridin-2-(1H)-one (10 g.) in 30% (v/v) sulfuric acid (200 ml.) was heated to reflux, in an atmosphere of nitrogen, and was held at reflux until no further reaction occured (ca. 5-8 hrs.). After cooling, the solution was added slowly and carefully to an icecooled solution of sodium hydroxide (50% solution; 200 ml.). The mixture was allowed to stand overnight and was then filtered. The product was washed with water, dried in air and recrystallized from dimethylformamide/water, with charcoal treatment, to yield the product, m.p. 276°-277.5° C.

Workup

  1. temperatureto reflux, in an atmosphere of nitrogen
  2. temperatureat reflux until no further reaction
  3. custom(ca. 5-8 hrs.)
  4. temperatureAfter cooling
  5. filtrationwas then filtered
  6. washThe product was washed with water
  7. customdried in air
  8. customrecrystallized from dimethylformamide/water, with charcoal treatment
  9. customto yield the product, m.p. 276°-277.5° C.

Sources & evidence

ORD record
ord-20ddbc87567a49668411cdce65f7d606
Source dataset
uspto-grants-1987_07
Patent number
US04680297

Reaction notes

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