Potassium Carbonate → ethyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1708539Notes

Reaction equation

HRID 1708539 reaction equation
F[C:2]1[C:26]([F:27])=[C:25]([F:28])[C:24]([F:29])=[CH:23][C:3]=1[C:4]([C:6](=[CH:12][NH:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:19]([O:18][C:16]([N:14]([N:13]1[C:23]2[C:3](=[CH:2][C:26]([F:27])=[C:25]([F:28])[C:24]=2[F:29])[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]1)[CH3:15])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178472138HCID 178472138, compound

Product 1

HCID 18959446ethyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-(2-tert-butoxycarbonyl-2-methylhydrazino)acrylate (10.50 g)and potassium carbonate (3.80 g)in dimethylformamide (31.5 ml)was heated at 60°~65° C. for one hour. The mixture was poured into ice-water (300 ml) to give a solid. The solid was filtered , dissolved in dichloromethane (100 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give a residue. The residue was triturated with n-hexane to give ethyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (9.25 g).

Workup

  1. temperaturewas heated at 60°~65° C. for one hour
  2. customto give a solid
  3. filtrationThe solid was filtered
  4. dissolutiondissolved in dichloromethane (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue
  8. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-60a02b26698f41849b5032a45d37ba60
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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