Triethylamine → 4-Methyl-7-(trifluoromethyl)-2-(trifluoromethylsulfonyl-oxy)quinoline-3-carboxylic acid ethyl ester

HRID 2093720Notes

Reaction equation

HRID 2093720 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH2:16]([O:18][C:19]([C:21]1[C:22](O)=[N:23][C:24]2[C:29]([C:30]=1[CH3:31])=[CH:28][CH:27]=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=2)=[O:20])[CH3:17].CCN(CC)CC>C(Cl)Cl>[CH2:16]([O:18][C:19]([C:21]1[C:22]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[N:23][C:24]2[C:29]([C:30]=1[CH3:31])=[CH:28][CH:27]=[C:26]([C:32]([F:35])([F:33])[F:34])[CH:25]=2)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178470056HCID 178470056, compound

Product 1

HCID 866626824-Methyl-7-(trifluoromethyl)-2-(trifluoromethylsulfonyl-oxy)quinoline-3-carboxylic acid ethyl esterYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

840 μl (5.0 mmol) trifluoromethanesulphonic acid anhydride was added in drops at 0° C. to a solution of 1.0 g (3.3 mmol) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester and 930 μl (6.7 mmol) NEt3 in DCM (30 ml). After 4 h of stirring at RT, the mixture was diluted with DCM (30 ml) and washed with water, a sat. aq. NaHCO3 sol. and brine. The organic phase was dried over Na2SO4 and concentrated in a vacuum. 1.32 g (3.1 mmol, 92%) 4-methyl-7-(trifluoromethyl)-2-(trifluoromethyl-sulfonyloxy)quinoline-3-carboxylic acid ethyl ester was obtained as a residue. The raw product was further converted without additional purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-d1294bbd12ac4822a79e479e64587086
Source dataset
uspto-grants-2013_05
Patent number
US08445512B2

Reaction notes

Loading…