Hydrochloric Acid → 4-Bromo-6-methoxy-1,5-naphthyridine-3-carboxylic acid

HRID 2356309Notes

Reaction equation

HRID 2356309 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[Br:18])=[N:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)=[O:7])C.Cl>C1COCC1>[Br: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 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68454651Ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 675490654-Bromo-6-methoxy-1,5-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 N NaOH (300 mL, 600 mmol) was added dropwise over 30 min to a stirred solution of 4-bromo-6-methoxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (83.56 g, 268 mmol) in THF (835 mL). Stirring was continued overnight, at which time LC/MS showed that the saponification was complete. 2 N HCl was added to pH 6 and the THF was removed in vacuo. 2 N HCl was added to pH 2, then water (250 mL) was added, and the mixture was cooled thoroughly in ice. The solid was collected by suction filtration, washed with water and dried (first using a rotary evaporator at 50° C. and then under high vacuum at 50° C. overnight) to give the title compound (76.7 g, slightly over quantitative). This material was used without further purification.

Workup

  1. customthe THF was removed in vacuo
  2. addition2 N HCl was added to pH 2
  3. additionwater (250 mL) was added
  4. temperaturethe mixture was cooled thoroughly in ice
  5. filtrationThe solid was collected by suction filtration
  6. washwashed with water
  7. customdried (
  8. customa rotary evaporator at 50° C.

Sources & evidence

ORD record
ord-21bf09af42424831ba4af937dc00552b
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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