Water → 5-Bromo-8-naphtholactam

HRID 433096Notes

Reaction equation

HRID 433096 reaction equation
[NH:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2.[Br:14]Br.O>ClC(Cl)Cl>[Br:14][C:6]1[C:5]2[C:4]3[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:13])[C:3]=3[CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 67222benz(cd)indol-2(1H)-one

Product 1

HCID 7547635-Bromo-8-naphtholactamYield 95.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Benz[cd]indol-2(1H)-one (2.1 g, 12.4 mmol) was dissolved in 50 ml trichloromethane and cooled to 0° C. To this stirred and cooled solution was added dropwise bromine (0.64 ml, 12.4 mmol) within 5 minutes. The reaction was allowed to warm up to room temperature for 24 hours. The reaction mixture was then poured into water and extracted with trichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated to give 2.935 g product (95% yield).

Workup

  1. temperaturecooled solution
  2. temperatureto warm up to room temperature for 24 hours
  3. extractionextracted with trichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd9c28abd8194709b8c456a6f52074f3
Source dataset
uspto-grants-2003_12
Patent number
US06667303B1

Reaction notes

Loading…