Benzoyl Peroxide → HCID 15123261, compound

HRID 1196525Notes

Reaction equation

HRID 1196525 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>C(Cl)(Cl)(Cl)Cl>[N:30]1([CH2:1][C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31268PyrrolidineHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 15123261HCID 15123261, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 6-methyl-3-pyridinecarboxylate (0.43 g) N-bromosuccinimide (0.59 g) and benzoylperoxide (50 mg) in dry carbon tetrachloride (10 ml) was stirred at 22° and irradiated with a 200 w light bulb for 2 days. Pyrrolidine (2.4 ml) was added and after 15 min the solution was partitioned between dichloromethane (20 ml) and 2N sodium carbonate solution (20 ml). The organic phase was washed with water, saturated brine, dried and evaporated to leave an oil (0.68 g). The oil was purified by flash chromatography eluting with a mixture of dichloromethane, ethanol and ammonia (300:8:1) to give the title compound as an oil (0.22 g). T.l.c. silica (Dichloromethane:methanol: 0.88 ammonia 300:8:1) Rf 0.5.

Workup

  1. customirradiated with a 200 w light bulb for 2 days
  2. customwas partitioned between dichloromethane (20 ml) and 2N sodium carbonate solution (20 ml)
  3. washThe organic phase was washed with water, saturated brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-0a52e0caecd94c67997aa42279209218
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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