Ethyl Acetate → 4,4'-Dimethoxybenzophenone O-(3-ethoxycarbonyl-2-methoxyiminopropyl)oxime

HRID 1031645Notes

Reaction equation

HRID 1031645 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7](=O)[CH2:8][O:9][N:10]=[C:11]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:5])[CH3:2].Cl.[O:30]([NH2:32])[CH3:31].C(OCC)(=O)C>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([CH2:6][C:7](=[N:32][O:30][CH3:31])[CH2:8][O:9][N:10]=[C:11]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 140527694,4'-dimethoxybenzophenone O-(3-ethoxycarbonyl-2-oxopropyl)oxime

Product 1

HCID 538534414,4'-Dimethoxybenzophenone O-(3-ethoxycarbonyl-2-methoxyiminopropyl)oximeYield 96.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.85 g of the 4,4'-dimethoxybenzophenone O-(3-ethoxycarbonyl-2- oxopropyl)oxime as obtained in Example 1 was dissolved in 5 ml of pyridine and 1 g of methoxylamine hydrochloride was added thereto. Then the obtained mixture was stirred at room temperature. After two hours, the reaction mixture was poured into ethyl acetate, washed with diluted hydrochloric acid and then with a saturated saline solution and purified by silica gel chromatography. Thus 4 g of the title compound was obtained in the form of a colorless oily product.

Workup

  1. washwashed with diluted hydrochloric acid
  2. customwith a saturated saline solution and purified by silica gel chromatography

Sources & evidence

ORD record
ord-2cba2dc056924fe7b2b605d33e87a4b6
Source dataset
uspto-grants-1990_09
Patent number
US04954523

Reaction notes

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