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.CCCCCC>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 4
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, 183.01 mmol) is dissolved in methylene chloride (500 ml) and treated drop wise with a solution of bromotrichloromethane (54.43 g, 274.51 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 55.72 g, 366.02 mmol) 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 hr where TLC analysis (4:1 hexane:ethyl acetate) shows reaction completion. The reaction mixture is diluted with ethyl acetate and then washed successively with dilute aqueous hydrochloric acid and brine. The ethyl acetate phase is dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. The residue is purified by recrystallisation from hexane:ethyl acetate to give the title compound (47.13 g, 95%) as pale yellow crystals.
Workup
- additionAfter the addition
- customreaction completion
- washwashed successively with dilute aqueous hydrochloric acid and brine
- dry with materialThe ethyl acetate phase is dried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue is purified by recrystallisation from hexane
Sources & evidence
- ORD record
- ord-2e3dda96bff5463095f983533e17f6bf
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580785B2
Reaction notes
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