Sodium Hydroxide → 3-Bromo-5-ethylpyridine

HRID 2387018Notes

Reaction equation

HRID 2387018 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 62.3%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of NaOH (10 g, 0.25 mol), hydrazine monohydrate (10 mL) and 3-acetyl-5-bromopyridine (5 g, 25 mmol) suspended in diethylene glycol (18 mL) was heated to 140° C. for 6 hours. The mixture was cooled to room temperature and partitioned between H2O and ether. The ether extracts were dried over MgSO4 and concentrated to a clear oil. Flash column chromatography (0% to 15% EtOAc in hexanes) gave the product as a clear oil (2.9 g, 58%). 1H NMR (400 MHz, CDCl3): δ 1.26 (t, J=7.6 Hz, 3 H), 2.65 (d, J=7.6 Hz, 2 H), 7.67 (t, J=2.0 Hz, 1 H), 8.37 (d, J=1.8 Hz, 1 H), 8.51 (d, J=2.0 Hz, 1 H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between H2O and ether
  3. dry with materialThe ether extracts were dried over MgSO4
  4. concentrationconcentrated to a clear oil

Sources & evidence

ORD record
ord-6bf9406961194d9ebd1eddbc2cce1ba7
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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