Sodium Hydroxide → HCID 178465840, compound

HRID 128616Notes

Reaction equation

HRID 128616 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[N:12][C:13]=1[CH3:14])[N:10]=[CH:9][C:8]([C:15]([O:17]CC)=[O:16])=[C:7]2[OH:20])[CH3:2].[OH-].[Na+]>O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[N:12][C:13]=1[CH3:14])[N:10]=[CH:9][C:8]([C:15]([OH:17])=[O:16])=[C:7]2[OH:20])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469690Ethyl 6-ethoxy-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 178465840HCID 178465840, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 6-ethoxy-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate (10.0 g), 5M sodium hydroxide solution (200 ml), IMS (64 ml) and water (64 ml) was boiled under reflux for 2 hours. The mixture was cooled to ambient temperature and then filtered. The residue was dissolved in water, acidified to pH 5 with glacial acetic acid and filtered. The residue was triturated with hot IMS, cooled and filtered to give 6-ethoxy-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid, m.p. 259°-261° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationfiltered
  3. dissolutionThe residue was dissolved in water
  4. filtrationfiltered
  5. customThe residue was triturated with hot IMS
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6184b95f75804620a25fa60bded738f1
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

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