Hydroxyamine hydrochloride → HCID 73678879, compound

HRID 2412466Notes

Reaction equation

HRID 2412466 reaction equation
Cl.[NH2:2][OH:3].[C:4]1([CH2:10][C:11]([CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>N1C=CC=CC=1.C(O)C>[N:2](=[C:11]([CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13093757HCID 13093757, compound

Product 1

HCID 73678879HCID 73678879, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Procedure

A mixture of hydroxylamine hydrochloride (9 g.) and a solution of 1-phenyl-3-phthalimidoacetone (23.4 g.) in pyridine/ethanol (80 ml.-80 ml.) was stirred at ambient temperature for 3 days. The resulting solution was concentrated, the residue washed twice with a mixture of toluene and methylene chloride and dried. The residue was purified by column chromatography on activated silica gel using cyclohexane/EtOAc 7:3 v/v as eluant to give 2-oximino-1-phenyl-3-phthalimidopropane (7.35 g.) as a mixture of syn and anti isomers.

Workup

  1. concentrationThe resulting solution was concentrated
  2. washthe residue washed twice with a mixture of toluene and methylene chloride
  3. customdried
  4. customThe residue was purified by column chromatography on activated silica gel

Sources & evidence

ORD record
ord-f70de087bfbe4be79090714b26c5b1b4
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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