Azobisisobutyronitrile → HCID 58154533, compound

HRID 2359421Notes

Reaction equation

HRID 2359421 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1C(=O)[N:19](Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[NH2:12][C:3]1[C:2]([CH2:1][NH2:19])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Product 1

HCID 58154533HCID 58154533, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of methyl 3-methyl-2-nitrobenzoate (45.0 g, 0.23 mol) and NBS (45.0 g, 0.25 mol) in CCl4 (1500 mL) was added AIBN (1.2 g, 7.3 mmol) portion-wise under reflux. The mixture was refluxed (48 hours), and the solvent was removed in vacuo. The residue was purified by silica gel column chromatography (6% to 10% Ethyl acetate gradient in petroleum ether) to obtain methyl 2-amino-3-(aminomethyl)benzoate (9.0 g, 14% yield).

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was refluxed (48 hours)
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography (6% to 10% Ethyl acetate gradient in petroleum ether)

Sources & evidence

ORD record
ord-028e4a4a4a1540e2b7ee8bbec6ed880e
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

Loading…