Acetic Anhydride → 6-Acetoxy-2-phenyl-4-quinolinecarboxylic acid

HRID 1259867Notes

Reaction equation

HRID 1259867 reaction equation
[OH-].[Na+].O1CCCC1.C([O:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18]C=C(O)[CH:21]=2)[N:16]=[C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=1)=[O:12])C.[C:30]([O:33][C:34](=[O:36])[CH3:35])(=O)[CH3:31]>ClCCl>[C:34]([O:33][C:30]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:31]=1)[N:16]=[C:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:14]=[C:13]2[C:11]([OH:12])=[O:10])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67204819HCID 67204819, compound

Product 1

HCID 672039976-Acetoxy-2-phenyl-4-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An aqueous sodium hydroxide solution (0.3184 g/30.0 mL) was added to a tetrahydrofuran (30.0 mL) solution of 6-hydroxy-2-phenyl-4-quinolinecarboxylic acid ethyl ester (1.1120 g, 3.79 mmol) obtained above, and the mixture was stirred at room temperature for 3 hours. To the reaction solution, dichloromethane (30.0 mL) and acetic anhydride (2.0 mL) were added. The mixture was washed with water and saturated saline and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography to obtain the title compound (1.0903 mg, 3.55 mmol) as a pale yellow powder.

Workup

  1. customobtained above, and the mixture
  2. washThe mixture was washed with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f5d942d9d8144cf9b555e0dd8485c4ef
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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