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

HRID 1294386
Notes
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Reaction equation

HRID 1294386 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.[OH-].[Na+].Cl>O1CCCC1CO.O>[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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 2

HCID 962WaterSolvent
HCID 7360
Tetrahydrofurfuryl alcohol
Solvent

Procedure

A suspension of ethyl 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate from Step 1 (1 eq) in a mixture of tetrahydrofuran-methanol (0.15M) and 1N aqueous sodium hydroxide (2 eq) was heated at ca 50° C. with stirring for 20 minutes. After cooling, the mixture was diluted with water and acidified with 1N aqueous HCl. After stirring for 45 minutes, the precipitate was filtered, washed well with water and dried to afford the title acid as a cream-colored solid.

Workup

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

Sources & evidence

ORD record
ord-eae04945e74f412f8b8941d988cd0e57
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238706B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes