Benzyloxyamine hydrochloride → Methyl 2-[4-(1-benzyloxyiminoethyl)phenoxymethyl]phenylglyoxylate O-methyloxime

HRID 374309Notes

Reaction equation

HRID 374309 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH3:24])=[CH:19][CH:18]=1)[C:5]([O:7][CH3:8])=[O:6].Cl.[CH2:27]([O:34][NH2:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[N:35][O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:24])=[CH:19][CH:18]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 54461346methyl 2-(4-acetylphenoxymethyl)phenylglyoxylate O-methyloxime

Product 1

HCID 54543447Methyl 2-[4-(1-benzyloxyiminoethyl)phenoxymethyl]phenylglyoxylate O-methyloximeYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.3 g (0.016 mol) of methyl 2-(4-acetylphenoxymethyl)phenylglyoxylate O-methyloxime and 3.0 g (0.019 mol) of benzyloxyamine hydrochloride in 60 ml of methanol are stirred at room temperature for 24 hours. The mixture is then hydrolyzed with water and extracted with methyl tert-butyl ether. The organic phase is washed with water, dried and concentrated. 5.9 g (83%) of the title compound are obtained in the form of colorless crystals (melting point 104°-106° C., compound no. 590).

Workup

  1. extractionhydrolyzed with water and extracted with methyl tert-butyl ether
  2. washThe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2600b0dd71cf4f6d900ac66fbafea4f6
Source dataset
uspto-grants-1992_11
Patent number
US05166399

Reaction notes

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