Azobisisobutyronitrile → Ethyl 4-chloro-2-(1-bromoethyl)nicotinate

HRID 2372216Notes

Reaction equation

HRID 2372216 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH2:13][CH3:14])[N:5]=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH:13]([Br:15])[CH3:14])[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19902853Ethyl 4-chloro-2-ethylpyridine-3-carboxylate

Product 1

HCID 19902854Ethyl 4-chloro-2-(1-bromoethyl)nicotinate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of the above ethylnicotinate (5.45 g), N-bromosuccinimide (NBS) (5.50 g) and 2,2'-azobis(2-methylpropionitrile) (AIBN) (0.40 g) in carbon tetrachloride (50 ml) is heated under reflux for 2 hours, then cooled, filtered and concentrated in vacuo to give ethyl 4-chloro-2-(1-bromoethyl)-nicotinate.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8cd7413f6154ee082ebce9472397793
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

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