Hydrochloric Acid → 7-Amino-4-trifluoromethyl-2-quinolinone

HRID 2164517Notes

Reaction equation

HRID 2164517 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[F:9][C:10]([F:20])([F:19])[C:11](=O)[CH2:12][C:13](OCC)=[O:14].O.Cl>C(O)C.[Cl-].[Cl-].[Zn+2]>[NH2:7][C:3]1[CH:2]=[C:1]2[C:6]([C:11]([C:10]([F:20])([F:19])[F:9])=[CH:12][C:13](=[O:14])[NH:8]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7935M-PhenylenediamineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 1940697-Amino-4-trifluoromethyl-2-quinolinoneYield 31.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

m-Phenylenediamine (28.84 g, 0.26 mole), ethyl trifluoroacetoacetate (49.12 g, 0.26 mole), and ZnCl2 (44 g) were refluxed in 280 ml ethanol containing 10 ml isopropanol for 18 hours. The reaction mixture was poured into 1600 ml iced water containing 10 ml. conc. HCl and let stand at room temperature 2 hours. The solid was filtered, washed with water and air dried. The product was recrystallized from 800 ml boiling ethanol to give 18.63 g (31%) 7-amino-4-trifluoromethylquinolone (AFQ).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water and air
  3. customdried
  4. customThe product was recrystallized from 800 ml

Sources & evidence

ORD record
ord-124656f26e7945ab834160af1a6d8a83
Source dataset
uspto-grants-1985_03
Patent number
US04505852

Reaction notes

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