Azobisisobutyronitrile → HCID 15672392, compound

HRID 1078084Notes

Reaction equation

HRID 1078084 reaction equation
CC1C=C(C(OC)=O)C(C(OC)=O)=NC=1.BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:36][CH:37](Br)[C:38]1[CH:39]=[C:40]([C:48]([O:50][CH3:51])=[O:49])[C:41]([C:44]([O:46][CH3:47])=[O:45])=[N:42][CH:43]=1>C(Cl)(Cl)(Cl)Cl>[Br:36][CH2:37][C:38]1[CH:39]=[C:40]([C:48]([O:50][CH3:51])=[O:49])[C:41]([C:44]([O:46][CH3:47])=[O:45])=[N:42][CH:43]=1

Participants

6

Reactant 4

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 117458692,3-Pyridinedicarboxylic acid, 5-methyl-, 2,3-dimethyl ester2×HCID 15672391HCID 15672391, compound

Product 1

HCID 15672392HCID 15672392, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of dimethyl 5-methyl-2,3-pyridinedicarboxylate (30.0 g, 0.143 mol), N-bromosuccinimide (32.0 g, 0.18 mol) and 2,2'-azobisisobutyronitrile (0.9 g, 0.0055 mol) in carbon tetrachloride (200 mL) is heated at 80° C. for 1.5 hours. Additional 2,2'-azobisisobutyronitrile (0.9 g, 0.0055 mol) is added and the reaction mixture is heated at reflux for 2 hours, cooled to room temperature and filtered. The filter cake is washed with carbon tetrachloride. The filtrate and wash are combined, washed with water and concentrated in vacuo to give an oil. The oil is shown by HPLC to contain 57% of the title product, 16% dimethyl 5-methyl-2,3-pyridinedicarboxylate and 23% dimethyl 5-dibromomethyl-2,3-pyridinedicarboxylate.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. washThe filter cake is washed with carbon tetrachloride
  6. washThe filtrate and wash
  7. washwashed with water
  8. concentrationconcentrated in vacuo
  9. customto give an oil

Sources & evidence

ORD record
ord-2c40abd583c94340885c2e4fe10ad240
Source dataset
uspto-grants-1996_08
Patent number
US05545835

Reaction notes

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