Sodium Hydroxide → 2,6-Diethyl-pyridine

HRID 2387019Notes

Reaction equation

HRID 2387019 reaction equation
[OH-].[Na+].O.NN.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=O)[CH3:16])[N:10]=1)(=O)[CH3:7]>C(O)COCCO>[CH2:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[N:10]=1)[CH3:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 707902,6-Diacetylpyridine

Product 1

HCID 1367452,6-Diethyl-pyridineYield 58.3%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of NaOH (14.7 g, 0.37 mol), hydrazine monohydrate (15 mL) and 2,6-diacetylpyridine (6 g, 36.8 mmol) suspended in diethylene glycol (27 mL) was cautiously heated to 120° C. for 16 hours. The mixture was cooled to room temperature and partitioned between H2O and ether. The ether extracts were washed with 1 N NaOH, 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 1.29 (t, J=7.8 Hz, 3 H), 2.80 (d, J=7.8 Hz, 2 H), 6.97 (d, J=2.0 Hz, 2 H), 7.51 (t, J=7.6 Hz, 1 H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between H2O and ether
  3. washThe ether extracts were washed with 1 N NaOH
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to a clear oil

Sources & evidence

ORD record
ord-d4487174196449ac9ddab7a649ac60b9
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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