Azobisisobutyronitrile → HCID 14365629, compound

HRID 2166463Notes

Reaction equation

HRID 2166463 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[N:10]([C:20](=[O:22])[CH3:21])[C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[N:10]([C:20](=[O:22])[CH3:21])[C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][Br:23])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 56984503HCID 56984503, compound

Product 1

HCID 14365629HCID 14365629, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

10 g (33.8 mmol) of 9-acetyl-4-methyl-β-carboline-3carboxylic acid ethyl ester is combined in 500 ml of carbon tetrachloride with 12 g (67.4 mmol) of N-bromosuccinimide and one spatula tip of azobisisobutyronitril and heated to reflux for 1.5 hours while simultaneously exposing the reaction mixture to light. After cooling, the mixture is suctioned off from the succinimide, concentrated, and the residue is extracted by stirring with hot water and suctioned off. Yield: 10.64 g (84%) of 9-acetyl-4-bromomethyl-β-carboline-β-carboxylic acid ethyl ester, mp 188°-189° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. temperatureAfter cooling
  4. concentrationconcentrated
  5. extractionthe residue is extracted

Sources & evidence

ORD record
ord-b4bd2254a5dc47508b704470f3d5ff74
Source dataset
uspto-grants-1990_07
Patent number
US04945163

Reaction notes

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