Water → HCID 13934588, compound

HRID 2118685Notes

Reaction equation

HRID 2118685 reaction equation
O[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][CH:20]([OH:22])[CH3:21].O.C([O-])(=O)C.[Na+]>Br>[CH3:21][CH:20]1[O:22][C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[N:7][C:6]=3[N:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:4](=[O:18])[C:3]=2[CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 547178214-Hydroxy-3-(2-hydroxypropyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 13934588HCID 13934588, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-hydroxy-3-(2-hydroxypropyl)-1-phenyl-1,8-naphthyridin-2(1H)-one (8.9 g; 0.03 mole) in 47% HBr (90 ml.) was stirred in an atmosphere of nitrogen. The solution was heated to 90° C. for 41/2 hrs. then was allowed to cool, poured into water and was adjusted to pH 4.5 with sodium acetate. The product was filtered off, washed with water, dried in air and recrystallized from CHCl3 /isopropanol to yield the product, m.p. 223°-224° C.

Workup

  1. temperatureto cool
  2. filtrationThe product was filtered off
  3. washwashed with water
  4. customdried in air
  5. customrecrystallized from CHCl3 /isopropanol
  6. customto yield the product, m.p. 223°-224° C.

Sources & evidence

ORD record
ord-7bc4d7bd4ec049caba028039f3cabd75
Source dataset
uspto-grants-1987_07
Patent number
US04680297

Reaction notes

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