Bromotrichloromethane → 5-Hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=[CH:9][C:8]=2[C:7](=[O:19])[CH2:6]1)=[O:4].BrC(Cl)(Cl)Cl.N12CCCN=C1CCCCC2>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([F:18])([F:16])[F:17])=[N:12]2)=[C:7]([OH:19])[CH:6]=1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-oxo-2-trifluoromethyl-5,6,7,8-tetrahydro-quinoline-7-carboxylic acid methyl ester (50.0 g) is dissolved in methylene chloride (500 mL) and treated drop wise with a solution of bromotrichloromethane (54.43 g) and 1,8-diazabicylo[5.4.0]undec-7-en (55.72 g) in methylene chloride (100 mL) at 0-5° C. After the addition is complete, the reaction mixture is allowed to warm to room temperature, and stirred for 1 h. The reaction mixture is diluted with ethyl acetate and then washed successively with diluted aqueous hydrochloric acid and brine. The ethyl acetate phase is dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue is purified by recrystallization from hexane/ethyl acetate to give 47.13 g of the title compound of the formula
Workup
- additionAfter the addition
- washwashed successively with diluted aqueous hydrochloric acid and brine
- dry with materialThe ethyl acetate phase is dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuum
- customThe residue is purified by recrystallization from hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-58360df6e7964d1a86fa984202de6f98
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247431B2
Reaction notes
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