Triethylamine → 6-Methoxy-3-trifluoromethanesulfonyloxy-quinoline-4-carboxylic acid methyl ester

HRID 2273185Notes

Reaction equation

HRID 2273185 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][C:21]=1O)=[O:19].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[CH3:16][O:17][C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][C:21]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 46912076Methyl 3-hydroxy-6-methoxyquinoline-4-carboxylate

Product 1

HCID 866715286-Methoxy-3-trifluoromethanesulfonyloxy-quinoline-4-carboxylic acid methyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (3.35 mL, 19.94 mmol, 1.5 eq) is added at room temperature to a stirred solution of 3-hydroxy-6-methoxy-quinoline-4-carboxylic acid methyl ester (3.1 g, 13.29 mmol, 1.0 eq) in dichloromethane (30 mL), followed by triethylamine (5.6 mL, 39.88 mmol, 3.0 eq). After 1 hour stirring at room temperature, solvent is removed and the residue is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1, v/v) to afford 6-methoxy-3-trifluoromethanesulfonyloxy-quinoline-4-carboxylic acid methyl ester as a yellow solid (3.69 g, 76% yield).

Workup

  1. customsolvent is removed
  2. customthe residue is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-22fc3ae141f643aab57fd5dc145fab0c
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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