Hexane → HCID 86757955, compound

HRID 842212Notes

Reaction equation

HRID 842212 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:5](=O)[CH3:6].O.[NH2:16][NH2:17].CCCCCC>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:5](=[N:16][NH2:17])[CH3:6]

Participants

5

Reactant 3

HCID 8058HexaneHCID 24654Hydrazine hydrate (1:1)HCID 54443146HCID 54443146, compound

Product 1

HCID 86757955HCID 86757955, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.12 g of 1-(4-chlorophenyl)-propane-1,2-dione-1-(O-methyloxime) in 20 ml of ethanol is mixed with 4 ml of hydrazine hydrate. After stirring for 21 hours at room temperature, 80 ml of hexane are added. The precipitated crystals are filtered off, washed with a little hexane and dried. In this way, 4.5 g of 1-(4-chlorophenyl)-2-hydrazono-propan-1-one O-methyloxime are obtained as white crystals having a melting point of 118-119° C. A solution of 3.06 g of the above substance and 3.0 g of (2-formylphenyl)-methoxyimino-acetic acid methyl ester (EP 621277) in 30 ml of pyridine is stirred for 18 hours at 90° C. After cooling, the reaction solution is poured onto ice water and the precipitated oil is extracted with ethyl acetate. Purification takes place with ethyl acetate/hexane (1:9) on silica gel, and the title compound is obtained as a viscous, yellow oil, which crystallises after some time. (melting point 104-105° C.).

Workup

  1. filtrationThe precipitated crystals are filtered off
  2. washwashed with a little hexane
  3. customdried

Sources & evidence

ORD record
ord-61de0fca87134e59a2ca8a355cfdf431
Source dataset
uspto-grants-2002_04
Patent number
US06372787B1

Reaction notes

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