3-Cyanopyridine → HCID 178513339, compound

HRID 908577Notes

Reaction equation

HRID 908577 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Cl.[NH2:10][OH:11].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>O>[OH:11][NH:10][C:1](=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 793-CyanopyridineHCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513339HCID 178513339, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Nicotinonitrile (1 g; 10 mmol) and 1.3 g of hydroxylamine hydrochloride (19 mmol) were dissolved in 15 ml of water. Sodium carbonate (2 g; 24 mmol) in 10 ml of water was continuously added, the resulting solution was stirred and heated at app. 70° C. for 6 hours. Then no more starting material was left (checked by TLC), the reaction mixture was cooled to room temperature, added sodium chloride until saturation and extracted 4 times with 50 ml of ethyl acetate. The organic layer was dried with sodium sulfate and evaporated to a solid. Yield 1 g (76%) of white solid powder.

Workup

  1. temperatureheated at app
  2. waitwas left (checked by TLC)
  3. extractionextracted 4 times with 50 ml of ethyl acetate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. customevaporated to a solid

Sources & evidence

ORD record
ord-f2f795451c1a4e75b22d80964e2f0551
Source dataset
uspto-grants-2011_09
Patent number
US08017631B2

Reaction notes

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