Hydroxyamine hydrochloride → 1-[2-(4-Chloro-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-piperidinone Oxime

HRID 1058628Notes

Reaction equation

HRID 1058628 reaction equation
[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[NH2:31][OH:32].C([O-])(=O)C.[Na+]>CO>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][C:20](=[N:31][OH:32])[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 186687451-[2-(4-Chloro-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-piperidinone

Product 1

HCID 186687711-[2-(4-Chloro-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-piperidinone OximeYield 120.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.20 g of 1-[2-(4-chloro-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-piperidinone, 0.04 g of hydroxylamine hydrochloride, 0.09 g of sodium acetate and 4 ml of methanol was stirred at room temperature for 1 hour. The reaction solution was concentrated, and the residue was added with aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, and dried, and the solvent was evaporated to give 0.25 g of a colorless solid. Recrystallization from ethyl acetate gave colorless crystals having the melting point of from 201 to 207° C. (decomposition).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was added with aqueous sodium hydrogencarbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution
  5. customdried
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-25617f0bc50d4fb995262c8267a26869
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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