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

HRID 1029788Notes

Reaction equation

HRID 1029788 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-847475eb3fa74d7c9321b1c4d0d1ddb1
Source dataset
uspto-grants-1992_04
Patent number
US05103010

Reaction notes

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