Trifluoroacetic acid → HCID 23154019, compound

HRID 1175793Notes

Reaction equation

HRID 1175793 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5](CC2C=CC(OC)=CC=2)[C:4](=[O:25])[C:3]=1[C:26]#[N:27].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[NH:5][C:4](=[O:25])[C:3]=1[C:26]#[N:27]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 10340Sodium CarbonateHCID 62406Trifluoromethanesulfonic acidHCID 23153957HCID 23153957, compound

Product 1

HCID 23154019HCID 23154019, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxy-1-(4-methoxybenzyl)2-oxo-1,2-dihydroquinoline-3-carbonitrile (300 mg), trifluoroacetic acid (5 ml), anisole (2 ml) and trifluoromethanesulfonic acid (1 ml) was stirred at room temperature for 1 day. After concentoration, the residue was cooled to 0° C. and ethyl acetate was added. The pH was adjusted to about 9 by adding 5% sodium carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate. The concentrated residue was purified with silica gel column chromatography to obtain the target compound (125 mg).

Workup

  1. temperatureAfter concentoration, the residue was cooled to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe concentrated residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-5f23514c8d2e4c2fae1dfeec0bb1ce30
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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