Ammonia → 2-Amino-4-methylpyridine-3-carbonitrile

HRID 1078222Notes

Reaction equation

HRID 1078222 reaction equation
[C:1]([C:3]([C:11]#[N:12])=[CH:4][C:5]([CH3:10])=COCC)#[N:2].[C:13](C(C#N)=CC(C)C(OCC)OCC)#N.[NH3:28]>>[NH2:28][C:11]1[C:3]([C:1]#[N:2])=[C:4]([CH3:13])[CH:5]=[CH:10][N:12]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 197072091,1-Dicyano-4,4-diethoxy-3-methyl-1-buteneHCID 542610241,1-Dicyano-4-ethoxy-3-methyl-1,3-butadiene

Product 1

HCID 103968872-Amino-4-methylpyridine-3-carbonitrile

Procedure

A solution of about 6.1 grams (0.038 mole) of a mixture of 1,1-dicyano-4-ethoxy-3-methyl-1,3-butadiene and 1,1-dicyano-4,4-diethoxy-3-methyl-1-butene in 200 mL of saturated methanolic ammonia is stirred at ambient temperature for about 15 hours. After this time the solvent is removed under reduced pressure, and the residue is partitioned between 160 mL of aqueous 1N hydrochloric acid and 160 mL of ethyl acetate. The aqueous layer is separated and poured into 160 mL of an aqueous solution saturated with sodium bicarbonate. The resultant solid is collected by filtration and dried, yielding about 2.6 grams of 2-amino-3-cyano-4-methylpyridine. Steps A and B are repeated.

Workup

  1. customAfter this time the solvent is removed under reduced pressure
  2. customthe residue is partitioned between 160 mL of aqueous 1N hydrochloric acid and 160 mL of ethyl acetate
  3. customThe aqueous layer is separated
  4. additionpoured into 160 mL of an aqueous solution saturated with sodium bicarbonate
  5. filtrationThe resultant solid is collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-46bee06820ae43059554c94acc80c471
Source dataset
uspto-grants-1996_08
Patent number
US05547954

Reaction notes

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