Triethylamine → 3-Chloropyridine-2-carbonitrile

HRID 723722Notes

Reaction equation

HRID 723722 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 (2.59g, 20 mmol), trimethylsilyl cyanide (5.95g, 60 mmol), and triethylamine (4.05g, 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 chomatography using 5% ether/CH2Cl2 as the eluent gave compound 775B (1.84g, 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 chomatography

Sources & evidence

ORD record
ord-3252c492a11c48478eb1eb4c8d8814b9
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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