Sodium Hydroxide → 3-Carboxy-8-nitro-4-oxo-3,4-dihydroquinoline

HRID 1416938Notes

Reaction equation

HRID 1416938 reaction equation
C([O:3][C:4]([CH:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7]1)=[O:5])C.[OH-].[Na+]>C(O)(=O)C>[C:4]([CH:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7]1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21250014Ethyl 8-nitro-4-oxo-3,4-dihydroquinoline-3-carboxylate

Product 1

HCID 212500243-Carboxy-8-nitro-4-oxo-3,4-dihydroquinolineYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-ethoxycarbonyl-8-nitro-4-oxo-3,4-dihydro-quinoline (12 g) and 2M sodium hydroxide solution (100 ml) was stirred at reflux for 1 hour. The mixture was cooled to ambient temperature and acidified to pH 5 with glacial acetic acid. The mixture was filtered and the solid so obtained washed with water to give 3-carboxy-8-nitro-4-oxo-3,4-dihydroquinoline in 93% yield, mp 263-265° C.

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationThe mixture was filtered
  3. customthe solid so obtained
  4. washwashed with water

Sources & evidence

ORD record
ord-c95134a8ec684c52b42244ff108741b8
Source dataset
uspto-grants-1999_06
Patent number
US05916898

Reaction notes

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