Triethylamine → 3-Chloropyridine-2-carbonitrile

HRID 2378466Notes

Reaction equation

HRID 2378466 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si]([C:13]#[N:14])(C)C.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[C:3]([C:13]#[N:14])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 123133Pyridine, 3-chloro-, 1-oxide

Product 1

HCID 8182583-Chloropyridine-2-carbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chloropyridine-1-oxide (2.59 g, 20 mmol), trimethylsilyl cyanide (5.95 g, 60 mmol), and triethylamine (4.05 g, 40 mmol) were combined in 40 mL of acetonitrile and reacted as described in example 763A. The solvent was removed in vacuo and the residue partitioned between CH2Cl2 and 3M potassium carbonate. The organic layer was separated, washed with brine, dried (MgSO4), and concentrated in vacuo. Purification of the crude product by silica gel chromatography using 5% ether/CH2Cl2 as the eluent gave compound 775B (1.84 g, 67%) as a white crystalline solid. HPLC: 100% at 1.64 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 139.0 [M+H]+.

Workup

  1. customreacted
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between CH2Cl2 and 3M potassium carbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-e8a9c5d3fbf347839329f1839ffd7e35
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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