Sodium Hydroxide → 5-Bromo-2-methyl-3-nitropyridine

HRID 1404572Notes

Reaction equation

HRID 1404572 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:19]([O-:21])=[O:20])[C:5]([CH:8](C(OCC)=O)C(OCC)=O)=[N:6][CH:7]=1.[OH-].[Na+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]([N+:19]([O-:21])=[O:20])[C:5]([CH3:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57516275Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate

Product 1

HCID 250672665-Bromo-2-methyl-3-nitropyridineYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

diethyl (5-bromo-3-nitropyridin-2-yl)propanedioate (6.8 g, 18.8 mmol) was refluxed in 290 ml of 6M HCl overnight. The reaction mixture was allowed to cool down to room temperature, and the mixture was neutralized with NaOH in an ice bath to pH 10. The solution was extracted with dichloromethane (DCM), dried, and evaporated to a yellow solid, 3.88 g, in 95% yield.

Workup

  1. extractionThe solution was extracted with dichloromethane (DCM)
  2. customdried
  3. customevaporated to a yellow solid, 3.88 g, in 95% yield

Sources & evidence

ORD record
ord-fc248d868acf419dab10fb4909d00e11
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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