Water → HCID 15457044, compound

HRID 1385919Notes

Reaction equation

HRID 1385919 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:25])[C:11](C(OCC)=O)=[C:12]([C:16]([F:19])([F:18])[F:17])[N:13]([CH3:15])[CH:14]=1.B(Br)(Br)Br.N1C2C(=CC=CC=2)C=CC=1.O>ClCCl.[Cu]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:25])[CH:11]=[C:12]([C:16]([F:19])([F:17])[F:18])[N:13]([CH3:15])[CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7047QuinolineHCID 25134Boron tribromideHCID 18408318HCID 18408318, compound

Product 1

HCID 15457044HCID 15457044, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-60 °C

Procedure

4.1 g (10.4 mmol) of 5-(2,4-dichlorophenyl)-3-ethoxycarbonyl-1-methyl-2-trifluoromethyl-4(1H)-pyridone was dissolved in 100 ml of dichloromethane, and 10 ml of a dichloromethane solution of 3N boron tribromide was dropwise added thereto under cooling to −60° C. After stirring at room temperature for 3 hours, the reaction solution was poured into ice water, and precipitated crystals were collected by filtration and washed with water. They were dried under reduced pressure to obtain crude crystals. To 50 ml of quinoline, the crude crystals and 0.04 g (0.6 mmol) of copper were added, followed by stirring at 170° C. for 1 hour. This reaction solution was poured into water, and precipitated crude crystals were collected by filtration. The crude crystals were dissolved in a small amount of DMF, and insoluble matters were filtered off. Then, the filtrate was poured into water, and precipitated crystals were collected by filtration. The crystals were washed with water and then dried to obtain 0.9 g (yield: 26%) of the desired product. Melting point: 205-206° C.

Workup

  1. customprecipitated crystals
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customThey were dried under reduced pressure
  5. customto obtain crude crystals
  6. stirringby stirring at 170° C. for 1 hour
  7. customprecipitated crude crystals
  8. filtrationwere collected by filtration
  9. dissolutionThe crude crystals were dissolved in a small amount of DMF, and insoluble matters
  10. filtrationwere filtered off
  11. additionThen, the filtrate was poured into water
  12. customprecipitated crystals
  13. filtrationwere collected by filtration
  14. washThe crystals were washed with water
  15. customdried

Sources & evidence

ORD record
ord-8a92fd0b52da4421aa921682a9a69ab6
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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