Diethyl (ethoxymethylene)malonate → HCID 86736427, compound

HRID 614772Notes

Reaction equation

HRID 614772 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([NH:6][CH2:7][C:8]([F:11])([F:10])[F:9])=[C:4]([CH3:14])[CH:3]=1.C([O:17][CH:18]=[C:19]([C:25](OCC)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>>[F:1][C:2]1[CH:13]=[C:12]2[C:5](=[C:4]([CH3:14])[CH:3]=1)[N:6]([CH2:7][C:8]([F:9])([F:10])[F:11])[CH:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]2=[O:17]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 21327122HCID 21327122, compound

Product 1

HCID 86736427HCID 86736427, compoundYield 42.8%

Procedure

A mixture of 66.1 g of 4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl)aniline and 75.0 g of diethyl ethoxymethylenemalonate was heated at 160° for 20 hours. Eight hundred grams of polyphosphoric acid (ca. 400 ml) was added and the resulting mixture heated at 105°-115° for 20 minutes. The hot reaction mass was poured onto 1 kg of cracked ice to hydrolyze the polyphosphoric acid; the resulting solid was filtered and recrystallized from acetonitrile to yield 45.2 g of 6-fluoro-1,4-dihydro-8-methyl-4-oxo-1-(2,2,2-trifluoroethyl)-3-quinolinecarboxylic acid, ethyl ester, m.p. 154°-158°.

Workup

  1. temperaturewas heated at 160° for 20 hours
  2. temperaturethe resulting mixture heated at 105°-115° for 20 minutes
  3. filtrationthe resulting solid was filtered
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-1556b40dc45d4d48b08e8c584f700b5c
Source dataset
uspto-grants-1979_03
Patent number
US04146625

Reaction notes

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