Potassium Carbonate → 1-Benzyl-3-(hydroxyimino)-4-methylpyrrolidine

HRID 358908Notes

Reaction equation

HRID 358908 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[C:10](=[N:16][OH:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 124309801-Benzyl-4-methylpyrrolidin-3-one

Product 1

HCID 859932571-Benzyl-3-(hydroxyimino)-4-methylpyrrolidineYield 107.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 31.7 g (0.168 mole) of 1-benzyl-4-methyl-3-pyrrolidone [prepared as described in Step (4) above] dissolved in 200 ml of ethanol was added dropwise to a solution of 59.4 g (0.79 mole) of hydroxylamine hydrochloride dissolved in 200 ml of water over a period of 1 hour, whilst keeping the temperature at 20° to 25° C. 62.1 g (0.45 mole) of potassium carbonate were then added, and the mixture was stirred at room temperature overnight, after which it was diluted with 100 ml of water. The aqueous solution was extracted with chloroform, and the chloroform extract was washed with water, dried and concentrated by evaporation under reduced pressure, to give 36.9 g of 1-benzyl-3-(hydroxyimino)-4-methylpyrrolidine as brown crystals.

Workup

  1. customat 20° to 25° C
  2. extractionThe aqueous solution was extracted with chloroform
  3. extractionthe chloroform extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fac065dec23f4efab27fae3f72637d10
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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