Benzoyl Peroxide → HCID 67995475, compound

HRID 72646Notes

Reaction equation

HRID 72646 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([CH3:12])=[CH:5][N:4]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:12][C:6]1[CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:3]([O:2][CH3:1])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 269676032-Methoxy-5-methyl-3-nitropyridine

Product 1

HCID 67995475HCID 67995475, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a well stirred solution of 2-methoxy-5-methyl-3-nitro-pyridine (8.4 g, 0.05 mol) in carbon tetrachloride (100 mL), benzoyl peroxide (3.5 g, 0.015 mol) and N-bromosuccinimide (17.8 g, 0.1 mol) were added. The reaction mixture was heated at reflux for 48 h under N2 atmosphere. After cooling, the mixture was evaporated. The residue was diluted with saturated aq. Na2CO3 (200 mL) and extracted (3×50 mL CH2Cl2). The combined extracts were washed with brine, dried on MgSO4, and filtered to yield an orange oil-like solid (8.3 g). Purification by chromatography over silica gel eluting with EtOAc/Petroleum ether (0:1 to 1:99 v/v) afforded product as a pale yellow solid. (4.1 g, 43%). 1H-NMR (CDCl3): δ 4.15 (s, 3H, OCH3), 4.51 (s, 2H, CH2), 8.34 (d, 1H, J=2.4 Hz, Py-H), 8.43 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (CDCl3): δ 27.72, 55, 17, 127.18, 133.66, 135.67, 151.40, 156.30.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 h under N2 atmosphere
  3. temperatureAfter cooling
  4. customthe mixture was evaporated
  5. additionThe residue was diluted with saturated aq. Na2CO3 (200 mL)
  6. extractionextracted (3×50 mL CH2Cl2)
  7. washThe combined extracts were washed with brine
  8. customdried on MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-3eb51190774c4b7e89b4141b3029f5cf
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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