Hydrochloric Acid → 5-Bromo-2-methyl-3-nitropyridine

HRID 1892194Notes

Reaction equation

HRID 1892194 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>O>[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 313Hydrochloric AcidHCID 57516275Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate

Product 1

HCID 250672665-Bromo-2-methyl-3-nitropyridineYield 88.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

To diethyl (5-bromo-3-nitropyridin-2-yl)malonate (66 g, 0.18 mol) was added water (250 mL) and 12 M HCl (360 mL, 4.32 mol). The mixture was heated at 105° C. until TLC showed starting material was consumed. The reaction mixture was then allowed to cool to rt and brine (0.67 L) was added. The organic solution was separated and the aqueous solution was extracted with DCM (3×0.67 L). The organic solutions were combined, washed with brine, sat. aq. NaHCO3, and brine again, dried over Na2SO4, filtered and concentrated to give 5-bromo-2-methyl-3-nitropyridine (34.7 g, 75%) as a yellow solid.

Workup

  1. customwas consumed
  2. temperatureto cool to rt
  3. additionbrine (0.67 L) was added
  4. customThe organic solution was separated
  5. extractionthe aqueous solution was extracted with DCM (3×0.67 L)
  6. washwashed with brine, sat. aq. NaHCO3, and brine again
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-96b9ca06b3134283a08b0c068c4c67e9
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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