Trimethylsilyldiazomethane → 2-Chloro-3-methoxy-4-nitropyridine

HRID 1811552Notes

Reaction equation

HRID 1811552 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][N:3]=1.[CH3:12][Si](C=[N+]=[N-])(C)C>C(#N)C.CO>[Cl:1][C:2]1[C:7]([O:8][CH3:12])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 217660172-Chloro-4-nitropyridin-3-ol

Product 1

HCID 138731102-Chloro-3-methoxy-4-nitropyridineYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-4-nitro-pyridin-3-ol (1.05 g, 6.02 mmol) in acetonitrile (45 mL) and methanol (5 mL), trimethylsilyldiazomethane (2M in hexane, 3.9 mL, 7.8 mmol) were added slowly. After 30 minutes, mixture was concentrated and residue was purified by column chromatography on silica gel (hexane/ethyl acetate 5:1) to give 2-chloro-3-methoxy-4-nitro-pyridine as a white solid (0.77 g, 68%). 1HNMR (CDCl3, 400 MHz) δ 8.35-8.34 (d, J=5.1 Hz, 1H), 7.58-7.56 (d, J=5.2 Hz, 1H), 4.08 (s, 3H).

Workup

  1. concentrationmixture was concentrated
  2. customresidue was purified by column chromatography on silica gel (hexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-922f03e42cff4eb7acc76c800b026f73
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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