Sulfuric Acid → 5-Hydroxypyridine-2-carbonitrile

HRID 406516

Reaction equation

HRID 406516 reaction equation
S(=O)(=O)(O)O.N[C:7]1[CH:8]=[N:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1.N([O-])=[O:16].[Na+]>O.C(OCC)(=O)C>[OH:16][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[N:9][CH:8]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 38713955-Aminopyridine-2-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 214137735-Hydroxypyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Concentrated sulfuric acid (21.0 mL) was added to a suspension of 3-amino-6-cyanopyridine (5.00 g, 42.0 mmol) in water (75.0 mL), and then a 1.6 M aqueous solution of sodium nitrite (29.0 mL, 46.4 mmol) was slowly added dropwise thereto under ice water cooling. This suspension was stirred for 6 hours at 100° C. The reaction mixture was cooled to room temperature, and then was diluted with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1, v/v). Thus, the title compound was obtained.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-1d7052acebb94fe69e24479fd6e409ca
Source dataset
uspto-grants-2014_06
Patent number
US08754112B2

Linked notes

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