Methanol → 7-Methoxyquinoline-3-carboxylic acid

HRID 1865423Notes

Reaction equation

HRID 1865423 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([O:15]CC)=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1.CO.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([OH:15])=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21865246Ethyl 7-methoxyquinoline-3-carboxylate

Product 1

HCID 146728247-Methoxyquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step C (399 mg, mmol) in THF (6 mL) was added methanol (1 mL) followed by NaOH (5N, 1.5 mL). After stirring at room temperature for 18 hours the reaction was concentrated in vacuo. The residue was acidified with 1N HCl (10 mL). The solution was concentrated in vacuo and azeotroped with toluene (4×). This material was used in the next step without any further purification.

Workup

  1. concentrationwas concentrated in vacuo
  2. concentrationThe solution was concentrated in vacuo
  3. customazeotroped with toluene (4×)
  4. customThis material was used in the next step without any further purification

Sources & evidence

ORD record
ord-22146aec56cb4f5692070cd8f65af8cd
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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