Phosphorus oxychloride → 2-Chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

HRID 242113Notes

Reaction equation

HRID 242113 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](O)=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:24]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:24])=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470056HCID 178470056, compound

Product 1

HCID 866453402-Chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 15.0 g (50.1 mmol) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in POCl3 (46 ml) was heated to 100° C. for 2 h. After cooling of the RS to RT, it was diluted with EtOAc and neutralised with a sat. aq. NaHCO3 sol. The organic phase was separated and washed with brine, dried over MgSO4 and concentrated in a vacuum. 15.4 g (48.5 mmol, 97%) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained as a residue. The raw product was further converted without additional purification.

Workup

  1. customwas separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-d8fdf6a53da148c4891ad8ff55325ba5
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

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