Benzoyl Peroxide → HCID 19866635, compound

HRID 232083Notes

Reaction equation

HRID 232083 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[N:6]=[CH:5][CH:4]=[C:3]2[O:2][CH3:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 198667274-Methoxy-8-methylquinoline

Product 1

HCID 19866635HCID 19866635, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Methoxy-8-methylquinoline (346 mg, 2 mmole), N-bromosuccinimide (365 mg, 2.05 mmole) and benzoyl peroxide (10 mg) in CCl4 (8 ml) were heated under reflux for 2.5 hours. The mixture was cooled and the succinimide was filtered off. The filtrate was washed with dilute aqueous NaHCO3 (1×) and water (1×), dried (Na2SO4) and evaporated to yield the sub-title compound as a pale yellow solid which was recrystallised from petroleum ether-cyclohexane to give colourless needles.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe succinimide was filtered off
  4. washThe filtrate was washed with dilute aqueous NaHCO3 (1×) and water (1×)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-6c8b3713be954fefba762a4a29aaf18e
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Reaction notes

Loading…