Hydrochloric Acid → HCID 21956378, compound

HRID 989291Notes

Reaction equation

HRID 989291 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Cl:20])=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[Cl:20][C:11]1[CH:10]=[C:9]2[C:14]([C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][NH:8]2)=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12733852Ethyl 7-chloro-1,4-dihydro-6-nitro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 21956378HCID 21956378, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.0 g (40.5 mmol) of 7-chloro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (J. Med. Chem. 23, 1358 (1980)) and 60.0 mL of 2.5 N sodium hydroxide in 160.0 mL of ethanol is heated at reflux temperature for 1.5 hours. After allowing the reaction mixture to cool to room temperature, it is further cooled in an ice bath, brought to pH 4 with 4.0 N hydrochloric acid and stirred for 0.5 hour. The solid is collected by filtration, washed with water and dried in vacuo to yield 10.1 g of 7-chloro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid as a tan solid, mp 294-297° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1.5 hours
  3. temperatureit is further cooled in an ice bath
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ef4b4aa6f4154d1c95bd7ead7e94518e
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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