HCID 9797012, compound → HCID 178469611, compound

HRID 561169Notes

Reaction equation

HRID 561169 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:10][CH:11]=[C:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:9][C:6]1[C:7]([F:8])=[C:2]([F:1])[CH:3]=[C:4]2[C:5]=1[C:18]([OH:20])=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=[N:10]2

Participants

3

Reactant 1

HCID 9797012HCID 9797012, compound

Product 1

HCID 178469611HCID 178469611, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 3,4,5-trifluoroaniline (5.00 g, 34.0 mmol) and diethyl ethoxymethylenemalnate (5.00 mL, 34.0 mmol) was stirred at 120° C. for 1 h. After cooling, diisopropyl ether was added to the reaction mixture and the resulting precipitates were collected by filtration to give diethyl [[(3,4,5-trifluorophenyl)amino]methylene]malonate (8.02 g, 74%) as a white powder. A mixture of diethyl [[(3,4,5-trifluorophenyl)amino]methylene]malonate (7.83 g, 23.1 mmol) and diphenyl ether (20 mL) was stirred at 250° C. for 1 h. After cooling, the resulting precipitates were collected by filtration. The filtered precipitates were suspended in hexane, and then filtered to give ethyl 5,6,7-trifluoro-4-hydroxy-3-quinolinecarboxylate (6.27 g, 94%) as a pale yellow powder.

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. customThe filtered precipitates
  5. filtrationfiltered

Sources & evidence

ORD record
ord-716b3e36a63a476cae4527c4b3cf8019
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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