Boron tribromide → 10-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 1530971Notes

Reaction equation

HRID 1530971 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[CH:18][C:17](=[O:20])[C:8]4[CH:9]=[C:10]([O:15]C)[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[CH:18][C:17](=[O:20])[C:8]4[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2125288210-bromo-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-bromo-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (3.2 g) obtained in Example 58 was suspended in anhydrous methylene chloride (500 ml), and boron tribromide (25 g) was added dropwise at room temperature. The mixture was stirred at room temperature for 12 hours and the reaction mixture was poured into ice water (1 L) and the crystals precipitated were recovered by filtration. The methylene chloride layer of the filtrate was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The two types of crystals thus obtained were combined, and the above-described procedure was repeated. The reaction mixture was poured into ice water (1 L), and the crystals precipitated were recovered by filtration. The crude crystals obtained were washed with a mixed solution of chloroform and methanol at an elevated temperature and recovered by filtration to obtain the title compound (2.4 g, 78%).

Workup

  1. customthe crystals precipitated
  2. filtrationwere recovered by filtration
  3. washThe methylene chloride layer of the filtrate was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe two types of crystals thus obtained
  7. customthe crystals precipitated
  8. filtrationwere recovered by filtration
  9. customThe crude crystals obtained
  10. washwere washed with a mixed solution of chloroform and methanol at an elevated temperature
  11. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-df3f7bd262874c4880586c814416efaa
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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