Water → HCID 9820089, compound

HRID 581978Notes

Reaction equation

HRID 581978 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22]C)=[C:5]([OH:14])[C:6](=[O:13])[NH:7]2.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[OH:22])=[C:5]([OH:14])[C:6](=[O:13])[NH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 15411215HCID 15411215, compound

Product 1

HCID 9820089HCID 9820089, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 5,7-dichloro-4-(5-chloro-2-methoxyphenyl)-3-hydroxy-2(1H)-quinolinone (2.22 g, 6.0 mmol) [prepared in Example 1] in methylene chloride was added BBr3 (30 mL, 1.0M solution in methylene chloride, 5.0 equiv.) at -78° C. and the suspension became a clear solution. The solution was stirred under an argon atmosphere at -78° C. for 3 hours then at room temperature for an additional 20 hours. Distilled water (0.5 mL) was added dropwise and stirring continued for 10 minutes. The reaction mixture was evaporated under vacuum and the solid residue was suspended in water (100 mL), sonicated for 5 minutes then stirred for 10 minutes, filtered, washed with water (3×30 mL) and dried to yield 2.15 g (≈100%) of the title compound as a white solid: mp=297-299° C.;

Workup

  1. waitat room temperature for an additional 20 hours
  2. stirringstirring
  3. waitcontinued for 10 minutes
  4. customThe reaction mixture was evaporated under vacuum
  5. customsonicated for 5 minutes
  6. stirringthen stirred for 10 minutes
  7. filtrationfiltered
  8. washwashed with water (3×30 mL)
  9. customdried

Sources & evidence

ORD record
ord-3fcaebe9a94f454c8d2828dc24bb6cd7
Source dataset
uspto-grants-1999_07
Patent number
US05922735

Reaction notes

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