3-Cyanopyridine → HCID 178513339, compound

HRID 470647Notes

Reaction equation

HRID 470647 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)#[N:10].C1(C)C=CC=CC=1>C(O)(C)C>[OH:3][NH:2][C:9](=[NH:10])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1

Participants

6

Reactant 4

HCID 793-CyanopyridineHCID 1140TolueneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178513339HCID 178513339, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 5.012 g (72.1 mmol) of hydroxylamine hydrochloride in 55 mL of isopropyl alcohol, 8.8 g (105.7 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25° C. to 30° C. for 10-15 min. 5.0 g (48 mmol) of 3-cyanopyridine was added and stirred at 80° C. to 85° C. for 3-4 h. After completion of the reaction, the reaction mixture was cooled to 25° C. to 30° C., filtered and washed with 10 mL of isopropyl alcohol. The filtrate was collected and distilled to obtain a crude residue, which was chased with 5 mL of toluene to yield the title compound.

Workup

  1. stirringstirred at 80° C. to 85° C. for 3-4 h
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to 25° C. to 30° C.
  4. filtrationfiltered
  5. washwashed with 10 mL of isopropyl alcohol
  6. customThe filtrate was collected
  7. distillationdistilled
  8. customto obtain a crude residue, which

Sources & evidence

ORD record
ord-87244d46d6b44b14942e86a97660db16
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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