Sodium Hydroxide → HCID 19364926, compound

HRID 850789Notes

Reaction equation

HRID 850789 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:20])[CH:18]=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15]C)[CH:10]=3.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:20])[CH:18]=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([OH:15])[CH:10]=3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 21252869HCID 21252869, compound

Product 1

HCID 19364926HCID 19364926, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9-bromo-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (650 mg) produced in Example 116 was suspended in anhydrous methylene chloride (50 ml), and a solution of boron tribromide in methylene chloride (1M, 12 ml) was added dropwise at room temperature. The mixture was heated under reflux for 14 hours, and the reaction mixture was poured into 1N aqueous solution of sodium hydroxide (100 ml), and the crystals precipitated were recovered by filtration. The thus obtained crude crystals were washed with ethanol and ether in succession to obtain the title compound (380 mg, 61%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. customthe crystals precipitated
  4. filtrationwere recovered by filtration
  5. customThe thus obtained crude crystals
  6. washwere washed with ethanol and ether in succession

Sources & evidence

ORD record
ord-5815ce350c114c3cbd6835e08eb9e186
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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