Ethanol → HCID 2798034, compound

HRID 2072689Notes

Reaction equation

HRID 2072689 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.C(O)C>CCCCCC>[CH2:23]([O:22][C:20]([C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][NH:4][C:3]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=1[F:1])=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 6871Diethyl (ethoxymethylene)malonateHCID 97092,4-Difluoroaniline

Product 1

HCID 2798034HCID 2798034, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Into an appropriate reactor fitted with warming, cooling and stirring means, were poured 152.5 ml (1.5 mol) of 2,4-difluoroaniline and 425 ml (2.1 mol) of diethyl ethoxymethylenemalonate. The mixture was warmed at 90° to 100° C. for about three hours with evacuation of ethanol appearing in the condensation. This lead to a solid product which was treated with hexane, washed, crystallized from hexane and dried to give 356.5 g (yield 76.5%) of 1-(2,2-diethoxycarbonyl-vinylamino)-2,4-difluoro-benzene. Elemental analysis of the product showed a good correspondence with the formula C14H15NO4F2. 350 g (1.17 mol) of this product were poured into a reactor with 1 liter of diphenyloxide. The mixture was refluxed at 265°-270° C. for 11/2 hours with a subsequent evacuation of the ethanol produced during the cyclisation. After cooling to ambient temperature, there was obtained a residue which was treated with benzene and then with hexane, dried and recrystallized from methanol. This gave 239 g (yiel 80.7%) of 1,4-dihydro-3-ethoxycarbonyl-6,8-difluoro-4-oxo-quinoline, elemental analysis of which showed a good correspondence with the formula C12H9NO3F2.

Workup

  1. customInto an appropriate reactor fitted
  2. temperaturewith warming
  3. temperaturecooling
  4. washwashed
  5. customcrystallized from hexane
  6. customdried

Sources & evidence

ORD record
ord-03e9264c976a4bf6b02d3b410889af5b
Source dataset
uspto-grants-1990_04
Patent number
US04914110

Reaction notes

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