Benzoyl Peroxide → 2-Chloromethyl-1,6-naphthyridine

HRID 327408Notes

Reaction equation

HRID 327408 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1.[Cl:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:12][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 5890322-Methyl-1,6-naphthyridine

Product 1

HCID 191085252-Chloromethyl-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-methyl-1,6-naphthyridine (E. M. Hawes, J. Heteroc. Chem. 11(2), 151 (1974)) (3.8 g) in CCl4 (230 mL) were added N-chlorosuccinimide (4.2 g) and benzoylperoxide (320 mg). The mixture was brought to reflux with two 150-watt spotlights and irradiated for 4 hr. The mixture was then cooled to room temperature, evaporated to dryness, and chromatographed on flash silica gel using ethyl acetate:toluene (1:1) as eluant to give the title compound, 80% pure and used as is for the next step.

Workup

  1. temperatureto reflux with two 150-watt spotlights
  2. customirradiated for 4 hr
  3. customevaporated to dryness
  4. customchromatographed on flash silica gel

Sources & evidence

ORD record
ord-eb51386eccc447b5866a91f349b3ac5b
Source dataset
uspto-grants-1993_12
Patent number
US05273980

Reaction notes

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