Methanol → 1-(3-Bromo-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

HRID 351729Notes

Reaction equation

HRID 351729 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([O:21]CC)=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[OH-].[Na+]>O1CCCC1.O.Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([OH:21])=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11057804Ethyl 1-(3-bromophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 223919781-(3-Bromo-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate from Step 2 (52.5 g, 140.7 mmol) in a mixture of tetrahydrofuran (400 mL), methanol (400 mL) and 1N aqueous sodium hydroxide (280 mL) was heated at ca 50° C. with stirring for 20 minutes. After cooling, the mixture was diluted with water (300 mL) and 1N aqueous HCl (325 mL) was added. After stirring for 45 minutes, the precipitate was filtered, washed well with water and dried to afford the 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylic acid as a cream-colored solid.

Workup

  1. temperaturewas heated at ca 50° C.
  2. temperatureAfter cooling
  3. additionwas added
  4. stirringAfter stirring for 45 minutes
  5. filtrationthe precipitate was filtered
  6. washwashed well with water
  7. customdried

Sources & evidence

ORD record
ord-918fa11d986c4d79b36d89a8d037ec14
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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