Sodium Hydroxide → HCID 178524722, compound

HRID 2398934Notes

Reaction equation

HRID 2398934 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][N:12]=2)[N:7]=[CH:6][C:5]=1[C:14]([O:16]CC)=[O:15]>O>[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][N:12]=2)[N:7]=[CH:6][C:5]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469573HCID 178469573, compound

Product 1

HCID 178524722HCID 178524722, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 8.0 g. (0.2 mol.) of sodium hydroxide in 200 ml. of water is added 20.0 g. (0.0917 mol.) of ethyl 4-hydroxy-1,5-naphthyridine-3-carboxylate. The mixture is heated under reflux for 6 hours, and then the hot solution is treated with decolorizingcharcoal and then filtered hot. The filtrate is cooled to 25° C. andacidified to pH 3 with 6N hydrochloric acid. The mixture is then cooled in an ice-bath for 15 minutes and the precipitate is removed by filtration. The solid obtained is washed with water, followed by ether, followed by acetone, and dried. This affords 11.2 g. (64% yield) of 4-hydroxy-1,5-naphthyridine-3-carboxylic acid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 6 hours
  3. additionthe hot solution is treated with decolorizingcharcoal
  4. filtrationfiltered hot
  5. temperatureThe mixture is then cooled in an ice-bath for 15 minutes
  6. customthe precipitate is removed by filtration
  7. customThe solid obtained
  8. washis washed with water
  9. customdried

Sources & evidence

ORD record
ord-0fb2aaac05794a7e894dd4e6c70e82b5
Source dataset
uspto-grants-1977_05
Patent number
US04026881

Reaction notes

Loading…