Sodium Hydroxide → 2,6-Diaminopyridine-3-carbonitrile

HRID 1927228Notes

Reaction equation

HRID 1927228 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 204748872,6-Diaminopyridine-3-carboxamide

Product 1

HCID 218881622,6-Diaminopyridine-3-carbonitrileYield 74.2%

Conditions

Temperature
100 °C

Procedure

2,6-Diamino-nicotinamide (520 mg) described in Manufacturing Example 7-1 and phosphorus oxychloride (5.0 g) were stirred for 0.5 hour at 100° C. The reaction solution was added to 0° C. dilute aqueous sodium hydroxide, which was then extracted with ethyl acetate. The organic layer was concentrated and the residue was purified with NH silica gel column chromatography (ethyl acetate) to obtain the titled compound (340 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified with NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-7f886482509f4db68bfcb5fd94c37ebe
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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