Triethylamine → 3,5-Dichloro-2-cyanopyridine

HRID 1003397Notes

Reaction equation

HRID 1003397 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[Si]([C:14]#[N:15])(C)C.C(N(CC)CC)C>C(#N)C>[C:14]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1)#[N:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 2762233,5-Dichloropyridine 1-oxide

Product 1

HCID 27696993,5-Dichloro-2-cyanopyridineYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-Dichloropyridine-N-oxide (10.0 g, 61 mmol), trimethysilylcyanide (25 mL, 183 mmol) and triethylamine (17 mL, 122 mmol) combined in acetonitrile (60 mL) and heated to reflux for 6 hr. The solvent was evaporated and the residue was partitioned between diethyl ether and 5% aq. NaHCO3. The organic phase was dried (MgSO4), evaporated, and the product purified by chromatography over silica gel to yield 10.0 g (97%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.92 (d, 1H), 8.58 (d, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hr
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between diethyl ether and 5% aq. NaHCO3
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. customthe product purified by chromatography over silica gel

Sources & evidence

ORD record
ord-1ffe1df8022e46d7a437c83113c0bbca
Source dataset
uspto-grants-2000_04
Patent number
US06046207

Reaction notes

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