Sodium Hydroxide → 6-Ethoxy-4-hydroxy-1,5-naphthyridine-3-carboxylic acid

HRID 479857Notes

Reaction equation

HRID 479857 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]([C:14]([O:16]CC)=[O:15])[C:7]2=[O:19])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]([C:14]([OH:16])=[O:15])[C:7]2=[O:19])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 604651Ethyl 6-ethoxy-1,4-dihydro-4-oxo-1,5-naphthyridine-3-carboxylate

Product 1

HCID 133443746-Ethoxy-4-hydroxy-1,5-naphthyridine-3-carboxylic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-ethoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (2.98 g), 1N NaOH (50 mL) and ethanol (10 mL) was heated at reflux for 2 h. The reaction mixture was cooled in an ice bath, acidified, and the resulting precipitate collected, rinsed with water and dried to give 2.42 g of 6-ethoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid as a beige solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. customthe resulting precipitate collected
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-df0c7c38f8fe4bdf900986e1979d5f3a
Source dataset
uspto-grants-2003_11
Patent number
US06646124B2

Reaction notes

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