Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate → 5-Bromo-2-methyl-3-nitropyridine

HRID 539781Notes

Reaction equation

HRID 539781 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>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

3

Reactant 1

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

Product 1

HCID 250672665-Bromo-2-methyl-3-nitropyridineYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred mixture of diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (12.5 g, 34.6 mmol) in HCl (7 N in water, 200 mL) is heated at reflux for 18 hours. The mixture is cooled to room temperature and extracted with CH2Cl2 (3×200 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via chromatography using CH2Cl2 to afford the title compound (5.8 g, 84%) as a yellow solid: Rf 0.67 (CH2Cl2); LCMS (m/z)=217.1, 219.2 [M+H]+, tR=2.01 min.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. extractionextracted with CH2Cl2 (3×200 mL)
  4. customOrganic layer is collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude product is purified via chromatography

Sources & evidence

ORD record
ord-426d6431d46e4497954873ce543c36e5
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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