Hydrochloric Acid → 6-Cyano-2-phenyl-4-quinolinecarboxylic acid

HRID 1259869Notes

Reaction equation

HRID 1259869 reaction equation
[OH-].[Na+].O1CCCC1.C[O:9][C:10]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=2)[N:15]=[C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:13]=1)=[O:11].Cl>ClCCl>[C:22]([C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:13]=[C:12]2[C:10]([OH:11])=[O:9])#[N:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 672044376-Cyano-2-phenyl-4-quinolinecarboxylic acid methyl ester

Product 1

HCID 672048646-Cyano-2-phenyl-4-quinolinecarboxylic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An aqueous sodium hydroxide solution was added to a tetrahydrofuran (20.0 mL) solution of 6-cyano-2-phenyl-4-quinolinecarboxylic acid methyl ester (0.6354 g, 2.20 mmol) obtained above, and the mixture was stirred at room temperature for 3 hours. To the reaction solution, dichloromethane was added. The mixture was neutralized with 1 N hydrochloric acid, and then washed with water and saturated saline, and dried over anhydrous sodium sulfate. After that, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography to obtain the title compound (0.5852 g, 2.13 mmol) as a pale yellow powder.

Workup

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

Sources & evidence

ORD record
ord-816e450eea104891b1e6154575f19aeb
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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