Sodium Hydroxide → 4-Chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acid

HRID 2273233Notes

Reaction equation

HRID 2273233 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[Cl:18])=[N:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)=[O:7])C>O1CCCC1.O>[Cl:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[N:15]=2)[N:10]=[CH:9][C:8]=1[C:6]([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23209173Ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 672555724-Chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acidYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (5.86 g, 140.6 mmol, 2.5 eq) is added protionwise at room temperature to a stirred solution of 4-chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (15.0 g, 56.25 mmol, 1.0 eq) in tetrahydrofuran (150 mL) and water (80 mL). After 15 hours stirring at room temperature, tetrahydrofuran is removed, the aqueous layer is cooled down to 0° C. and the pH is adjusted to 3 by the addition of a 2N hydrochloric acid aqueous solution. The resulting precipitate is collected by filtration, washed with water and dried under high vacuum to afford 4-chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acid as a light red solid (12.9 g, 96% yield).

Workup

  1. customtetrahydrofuran is removed
  2. temperaturethe aqueous layer is cooled down to 0° C.
  3. additionthe pH is adjusted to 3 by the addition of a 2N hydrochloric acid aqueous solution
  4. filtrationThe resulting precipitate is collected by filtration
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-90cafb800b0849d6ac2a70e491527973
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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