Boron tribromide → 10-bromo-2-hydroxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 1530962Notes

Reaction equation

HRID 1530962 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([CH3:20])[C:17](=[O:21])[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]=[C:18]([CH3:20])[C:17](=[O:21])[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 2125282210-bromo-2-methoxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 2125284210-bromo-2-hydroxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-bromo-2-methoxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one (4.8 g) obtained in Example 48 was suspended in anhydrous methylene chloride (400 ml), and boron tribromide (25 g) was added dropwise to the suspension at room temperature. The mixture was stirred at room temperature for 12 hours and the reaction mixture was poured into ice water (1500 ml) and the crystals precipitated were recovered by filtration. The resulting crude crystals were washed with ether, and recovered by filtration to obtain the title compound (4.6 g, constant amount).

Workup

  1. customthe crystals precipitated
  2. filtrationwere recovered by filtration
  3. washThe resulting crude crystals were washed with ether
  4. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-f21368d1121d4c888110f0ce40a05896
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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