Sodium Hydroxide → 6-Methoxy-[1,5]naphthyridine-3-carboxylic acid

HRID 1422690Notes

Reaction equation

HRID 1422690 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[N:13][C:12]([O:16][CH3:17])=[CH:11][CH:10]=2)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:17][O:16][C:12]1[N:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:15]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66747245Ethyl 6-methoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 538928166-Methoxy-[1,5]naphthyridine-3-carboxylic acidYield 161.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-methoxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (32.0 g, 74.45 mmol, 1.0 eq) and sodium hydroxide (10.12 g, 137.51 mmol, 1.85 eq) in ethanol (110 mL) is refluxed for 3 hours. The solvent is evaporated and the residue is dissolved in water, washed with ethyl acetate, then acidified with 3N hydrochloric acid aqueous solution to pH=3-4. The precipitate is collected by filtration, dried under 50° C. overnight to afford 6-methoxy-[1,5]naphthyridine-3-carboxylic acid as a white solid (24.5 g, 82% yield).

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe solvent is evaporated
  3. dissolutionthe residue is dissolved in water
  4. washwashed with ethyl acetate
  5. filtrationThe precipitate is collected by filtration
  6. customdried under 50° C. overnight

Sources & evidence

ORD record
ord-629103996e8a4193977bf5fa3746922c
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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