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

HRID 1392690Notes

Reaction equation

HRID 1392690 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

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 962WaterSolventHCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A suspension of ethyl 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate from Step 2 (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-79dd0a88cc204d2f89cae9e54045cde1
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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