Sodium Hydroxide → 2-Cyano-5-fluoropyridine

HRID 2080473Notes

Reaction equation

HRID 2080473 reaction equation
N1C=CC=CC=1.[FH:7].N[C:9]1[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=1.N([O-])=O.[Na+].[OH-].[Na+]>CCCCCC>[F:7][C:9]1[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 64774Pyridine, hydrofluoride (1:1)HCID 38713955-Aminopyridine-2-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 113324532-Cyano-5-fluoropyridineYield 64%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To hydrogen fluoride-pyridine (100 ml) was added 5-amino-2-cyanopyridine (24.5 g, 0.206 mol) under ice cooling. The resulting mixture was stirred for 10 minutes. To the reaction mixture was added sodium nitrite (15.6 g, 0.226 mol). The resulting mixture was stirred at room temperature for 10 minutes, and then stirred at 50° C. for 2 hours. To the reaction mixture was added a 20% aqueous solution of sodium hydroxide. The resulting mixture was extracted with diethyl ether. The organic layer thus obtained was dried over sodium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure to give the title compound (16.0 g, 0.131 mmol, 64%) as colorless needle crystals.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 10 minutes
  2. stirringstirred at 50° C. for 2 hours
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c874691fe1d54ee6b4cca74cf91d7557
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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