5-Aminopyridine-2-carbonitrile → 5-Hydroxypyridine-2-carbonitrile

HRID 2377578Notes

Reaction equation

HRID 2377578 reaction equation
N[C:2]1[CH:3]=[N:4][C:5]([C:8]#[N:9])=[CH:6][CH:7]=1.N([O-])=[O:11].[Na+]>O.S(=O)(=O)(O)O>[C:8]([C:5]1[N:4]=[CH:3][C:2]([OH:11])=[CH:7][CH:6]=1)#[N:9]

Participants

5

Reactant 2

HCID 38713955-Aminopyridine-2-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 214137735-Hydroxypyridine-2-carbonitrileYield 63.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1 g (8.06 mmol) of 3-amino-6-cyanopyridine in 12 ml of water and 1.2 ml of sulfuric acid is cooled to 0° C. and 1 g (14.5 mmol) of sodium nitrite is added slowly. The reaction mixture is left to return to room temperature and then stirred at 100° C. for 3 hours. It is left to stand overnight in a refrigerator. The precipitate formed is filtered off and washed with iced water. The expected product also present in the filtrate is extracted with ethyl acetate and combined with the previous precipitate. This crude product is purified by chromatography on silica gel using a dichloromethane/methanol mixture (98/2; v/v) as the eluent to give 613 mg of the expected compound in the form of a brown powder (yield=63%).

Workup

  1. waitThe reaction mixture is left
  2. customto return to room temperature
  3. waitIt is left
  4. waitto stand overnight in a refrigerator
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed with iced water
  8. extractionThe expected product also present in the filtrate is extracted with ethyl acetate
  9. customThis crude product is purified by chromatography on silica gel using a dichloromethane/methanol mixture (98/2; v/v) as the eluent

Sources & evidence

ORD record
ord-ace070b3db7d44b7bf2df069440ed287
Source dataset
uspto-grants-2008_12
Patent number
US07470671B2

Reaction notes

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