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Water → 5,6-Dimethyl-2-methoxy-3-nitropyridine

HRID 489261
Notes
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Reaction equation

HRID 489261 reaction equation
C[O-].[Na+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([CH3:14])=[C:7]([CH3:15])[N:6]=1.[CH2:16]([O:18]CC)C.O>CO>[CH3:14][C:8]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]([O:18][CH3:16])=[N:6][C:7]=1[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 100811492-Chloro-5,6-dimethyl-3-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 222664775,6-Dimethyl-2-methoxy-3-nitropyridineYield 82.6%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent
2×

Conditions

Temperature
50 °C

Procedure

To a solution of 28% sodium methoxide (1.11 mL) and methanol (5.5 mL) was added dropwise a solution of 2-chloro-5,6-dimethyl-3-nitropyridine (1-013-05) (837 mg) in methanol (6.6 mL) for 5 min at room temperature under nitrogen atmosphere, and the reaction mixture was heated with stirring in oil-bath at 50° C. for 7 h. To the reaction mixture was added diethyl ether and the reaction mixture was poured into water, extracted with twice with diethyl ether, washed once with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 5,6-dimethyl-2-methoxy-3-nitropyridine (1-013-06) (675 mg, 82.6%, m.p.: 71-73° C.) as an orange crystal.

Workup

  1. temperaturethe reaction mixture was heated
  2. extractionextracted with twice with diethyl ether
  3. washwashed once with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d6adb4d951c04c2c803bc46bf27d74fd
Source dataset
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06977266B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes