2-Chloro-6-methoxy-3-nitropyridine → 6-Methoxy-2-(methylthio)-3-nitropyridine

HRID 2219259Notes

Reaction equation

HRID 2219259 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[CH3:13][S-:14].[Na+]>CO>[CH3:12][O:11][C:4]1[N:3]=[C:2]([S:14][CH3:13])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 225921666-Methoxy-2-(methylthio)-3-nitropyridineYield 60.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol (100 ml) solution of 2-chloro-6-methoxy-3-nitropyridine (2.0 g, 10.4 mmol) was added dropwise to a methanol (20 ml) solution of sodium thiomethoxide (805 mg, 10.9 mmol) while being cooled with ice, and the temperature thereof was raised to the room temperature and the mixed solution was stirred for 17 hours and the precipitated crystal was filtered to obtain 1.26 g (yield 59%) of 6-methoxy-2-methylthio-3-nitropyridine as a yellow powdery crystal,

Workup

  1. temperaturewhile being cooled with ice
  2. filtrationthe precipitated crystal was filtered

Sources & evidence

ORD record
ord-06174671abf24365badf5349db95daba
Source dataset
uspto-grants-2008_08
Patent number
US07414066B2

Reaction notes

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