Methanol → 2,3-Dimethoxy-5-nitropyridine

HRID 1042868Notes

Reaction equation

HRID 1042868 reaction equation
[Na].Cl[C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[CH:5][N:4]=1.[CH3:14][OH:15]>>[CH3:14][O:15][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545Sodium2×HCID 234561522-Chloro-3-methoxy-5-nitropyridine

Product 1

HCID 38487442,3-Dimethoxy-5-nitropyridine

Procedure

A round bottom flask was charged with methanol under nitrogen. Freshly cut sodium (91 mg, 3977 μmol) was added, and the mixture was stirred at RT under nitrogen until the sodium had dissolved. 2-Chloro-3-methoxy-5-nitropyridine (500 mg, 2652 μmol) was added and the reaction mixture was stirred under nitrogen at RT. After ˜15 min the mixture became heterogeneous and thick, and GC/MS analysis of a sample taken at 0.5 h indicated complete conversion to the desired product. The mixture was diluted with DCM and water and the layers were separated. The aqueous portion was extracted with additional DCM and the combined organics were dried, filtered and concentrated. The crude solid was passed through a silica plug using 5% MeOH/DCM. The filtrate was concentrated to provide 2,3-dimethoxy-5-nitropyridine as a light yellow solid. MS [M+H]=185.

Workup

  1. dissolutionhad dissolved
  2. waitthick, and GC/MS analysis of a sample taken at 0.5 h

Sources & evidence

ORD record
ord-5165749b11a34cbfb34bcc7c42cef931
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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