Acetic Acid → HCID 13387884, compound

HRID 615331Notes

Reaction equation

HRID 615331 reaction equation
[OH-].[Na+].[NH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11]([Cl:14])[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([O:19]CC)=[O:18])=[CH:5]1.C(O)(=O)C>O>[NH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11]([Cl:14])[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 3021288Ethyl 1-amino-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 13387884HCID 13387884, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.91 g, 0.0228 mole) was dissolved in 100 ml of water, and 2.6 g (0.0091 mole) of ethyl 1-amino-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate was added. The mixture was stirred on a steam bath for two hours and the hot solution was neutralized with acetic acid (1.6 ml). The suspension of solid was stirred at room temperature for about sixteen hours, and the solid was collected by filtration and washed with water. The product was recrystallized from dimethylformamide to give 2.0 g of 1-amino-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, beige powder, m.p. 312°-315° C.

Workup

  1. additionThe suspension of solid
  2. stirringwas stirred at room temperature for about sixteen hours
  3. filtrationthe solid was collected by filtration
  4. washwashed with water
  5. customThe product was recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-0803f56b7976477d9ba5e347dfe24260
Source dataset
uspto-grants-1985_02
Patent number
US04499091

Reaction notes

Loading…