Sodium Hydroxide → 2-Methyl-5-nitropyridine

HRID 1910752Notes

Reaction equation

HRID 1910752 reaction equation
C(OC(=O)[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1)C(OCC)=O)C.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:5][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2794558Diethyl 2-(5-nitropyridin-2-yl)malonate

Product 1

HCID 27945522-Methyl-5-nitropyridineYield 85.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

To 2-(5-nitro-pyridin-2-yl)-malonic acid diethyl ester (12.0 g, 42.5 mmol) was added cold aq. 20% sulfuric acid (120 mL) and the mixture was heated to 100° C. for 2 h. The cooled reaction was added to cold dilute sodium hydroxide solution and the pH adjusted to pH ˜10. The organics were extracted with dichloromethane (×4), then the combined organic phases were dried over sodium sulfate. The filtrate was concentrated to afford 2-methyl-5-nitro pyridine (5.0 g, 83%) as a brown solid.

Workup

  1. customThe cooled reaction
  2. extractionThe organics were extracted with dichloromethane (×4)
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-682ba14c50e14d7a87e94ecdb745dba4
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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