Sodium Hydroxide → 3-Bromo-5-ethylpyridine

HRID 858707Notes

Reaction equation

HRID 858707 reaction equation
[OH-].[Na+].O.NN.[C:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)(=O)[CH3:7]>C(O)COCCO>[Br:15][C:13]1[CH:12]=[N:11][CH:10]=[C:9]([CH2:6][CH3:7])[CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 8204233-Acetyl-5-bromopyridine

Product 1

HCID 6428043-Bromo-5-ethylpyridineYield 65%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
140 °C

Procedure

Sodium hydroxide (10 g, 0.25 mol) and hydrazine monohydrate (10 mL) were added to a solution of 3-acetyl-5-bromopyridine (5 g, 25 mmol) dissolved in diethylene glycol (18 mL). The reaction mixture was heated to 140° C. for 6 hours and then partitioned between H2O and Ether. The organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash silica gel chromatography (0% to 40% EtOAc in hexanes) to give the title compound (3 g, 65%). 1H NMR (400 MHz, CDCl3): δ 1.26 (t, J=7.6 Hz, 3 H), 2.65 (q, J=7.6 Hz, 2 H), 7.67 (s, 1 H), 8.37 (s, 1 H), 8.51 (s, 1 H).

Workup

  1. custompartitioned between H2O and Ether
  2. washThe organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash silica gel chromatography (0% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-42f065e7f3a04f07a1d5ffb502b73b68
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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