Sodium Hydroxide → HCID 19592883, compound

HRID 613521Notes

Reaction equation

HRID 613521 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[C:16]2[C:11](=[C:12]([NH:17][C:18](=[O:27])[C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([CH2:6][C:7]1[C:16]2[C:11](=[C:12]([NH:17][C:18](=[O:27])[C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19592759HCID 19592759, compound

Product 1

HCID 19592883HCID 19592883, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-ethoxycarbonylmethyl-8-(2,6-dichlorobenzoylamino)quinoline (1.03 g) in ethanol (6 ml) was added 1N-aqueous sodium hydroxide solution (3.83 ml), and the mixture was stirred at 50° C. for two hours. The organic solvent was removed in vacuo and the aqueous residue was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried and evaporated. The residue was crystallized spontaneously and it was triturated with ethyl acetate to give 4-carboxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (703 mg).

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe extract was dried
  4. customevaporated
  5. customThe residue was crystallized spontaneously
  6. customit was triturated with ethyl acetate

Sources & evidence

ORD record
ord-0a402c16ac8a4e06bfe6e85683b8d03b
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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