Benzoyl Peroxide → HCID 13769241, compound

HRID 2232508Notes

Reaction equation

HRID 2232508 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 103761391-methyl-3-phenylisoquinoline

Product 1

HCID 13769241HCID 13769241, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-methyl-3-phenylisoquinoline (21 g), N-bromosuccinimide (30.6 g) and benzoyl peroxide (1 g) in carbon tetrachloride (730 cc) is brought to boiling for 48 hours. After being cooled, the mixture is filtered and the filtrate evaporated to dryness under reduced pressure. The residue is chromatographed on silica gel with a toluene/methanol (98:2 by volume) mixture as eluant. After crystallization in isopropyl ether, 1-bromomethyl-3-phenylisoquinoline (11 g), m.p. 84° C., is obtained.

Workup

  1. temperatureAfter being cooled
  2. filtrationthe mixture is filtered
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. customThe residue is chromatographed on silica gel with a toluene/methanol (98:2 by volume) mixture as eluant
  5. customAfter crystallization in isopropyl ether

Sources & evidence

ORD record
ord-d74e2283d5e84a0e9533c72a86c5d293
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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