Ammonium Hydroxide → 2-Amino-3-cyanopyridine

HRID 557214Notes

Reaction equation

HRID 557214 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[NH4+:11]>>[NH2:11][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 810792-Chloronicotinonitrile

Product 1

HCID 8182592-Amino-3-cyanopyridine

Conditions

Temperature
120 °C

Procedure

Add 100 mL ammonium hydroxide to a sealed tube containing 12.5 gm (90.21 mMol) 2-chloro-3-cyanopyridine. Seal the tube and heat the suspension at 120° C. for 6 hours. Cool the reaction mixture to room temperature and partition between ethyl acetate and saturated aqueous sodium bicarbonate. Extract the aqueous phase with ethyl acetate (3×100 mL) followed by 70:30 ethyl acetate:n-butanol (2×100 mL). Combine organic phases and concentrate under reduced pressure to provide 2-amino-3-cyanopyridine.

Workup

  1. customSeal the tube
  2. temperatureCool the reaction mixture to room temperature
  3. custompartition between ethyl acetate and saturated aqueous sodium bicarbonate
  4. extractionExtract the aqueous phase with ethyl acetate (3×100 mL)
  5. concentrationCombine organic phases and concentrate under reduced pressure

Sources & evidence

ORD record
ord-0a38d3a7c014446c88a7a820163696c2
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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