Water → 1-[2-(Dimethylamino)-4-pyridinyl]ethanone oxime

HRID 1155546Notes

Reaction equation

HRID 1155546 reaction equation
Cl.[NH2:2][OH:3].O.[OH-].[Na+].[CH3:7][N:8]([CH3:18])[C:9]1[CH:14]=[C:13]([C:15](=O)[CH3:16])[CH:12]=[CH:11][N:10]=1>CO>[CH3:7][N:8]([CH3:18])[C:9]1[CH:14]=[C:13]([C:15](=[N:2][OH:3])[CH3:16])[CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 13145269HCID 13145269, compound

Product 1

HCID 1363591981-[2-(Dimethylamino)-4-pyridinyl]ethanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3.1 g. (45 mmoles) of hydroxylamine hyrochloride in 25 ml. of water and 22.5 ml. of 2 N sodium hydroxide solution was added 4.31 g. (26 mmoles) of 1-(2-dimethylamino-4-pyridyl)-1-ethanone, and the mixture was heated to boiling. After 5 minutes, methanol was added until the mixture became homogeneous. Heating was continued until a precipitate started to appear, and the mixture was then cooled. The solids were filtered, washed with water and dried. Recrystallization from toluene gave 4.03 g. (86%) of product, m.p. 145°-148° C.

Workup

  1. temperatureHeating
  2. temperaturethe mixture was then cooled
  3. filtrationThe solids were filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from toluene
  7. customgave 4.03 g

Sources & evidence

ORD record
ord-d29607b7a252432d9d9c354975af87ff
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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