Hydrochloric Acid → HCID 178516137, compound

HRID 1791953Notes

Reaction equation

HRID 1791953 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[F:9][C:10]([F:20])([F:19])[C:11](=O)[CH2:12][C:13](OCC)=[O:14].Cl>C1C=CC=CC=1>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[C:11]([C:10]([F:20])([F:19])[F:9])[CH:12]=[C:13]2[OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 95842-FluoroanilineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 178516137HCID 178516137, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
110 °C

Procedure

2-Fluoroaniline (10.0 g), ethyl trifluoroacetoacetate (16.6 g) and concentrated hydrochloric acid (0.1 mL) were dissolved in benzene (40 mL), and the mixture was refluxed in a reaction vessel equipped with Dean-Stark trap for 7 hr. The reaction mixture was concentrated under reduced pressure and 75% phosphoric acid (40 mL) was added thereto. The mixture was stirred at 110° C. for 5 hr. The reaction mixture was added to water, neutralized with sodium hydrogencarbonate, and extracted with ethyl acetate. The extract was concentrated under reduced pressure to give 8-fluoro-4-hydroxy-2-trifluoromethylquinoline (1.77 g).

Workup

  1. temperaturethe mixture was refluxed in a reaction vessel
  2. customequipped with Dean-Stark trap for 7 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure and 75% phosphoric acid (40 mL)
  4. additionwas added
  5. additionThe reaction mixture was added to water
  6. extractionextracted with ethyl acetate
  7. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-536255495e2a44b2857c9407963d2f6a
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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