Methanol → 7-Methoxyquinoline-3-carboxylic acid
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- concentrationwas concentrated in vacuo
- concentrationThe solution was concentrated in vacuo
- customazeotroped with toluene (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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