1-(4-Chlorophenyl)-2-(hydroxyimino)ethanone synthesis
- Product Name:1-(4-Chlorophenyl)-2-(hydroxyimino)ethanone
- CAS Number:3750-07-0
- Molecular formula:C8H6ClNO2
- Molecular Weight:183.59
99-91-2
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Yield:-
Reaction Conditions:
with hydrogenchloride;water;sodium nitrite at -15; for 0.75 h;
Steps:
Experimental procedure: A CEM Discover microwave (MW) reactor was used. The reactions were followed by TLC. The reaction time was determined based on several trials in each case. Two stage synthesis: Each α-oximino ketone was prepared from the corresponding ketone.[27] and [28] (a) Neat: 1,2-Diaminobenzene (0.37 g, 3.4 mmol) and the oximino ketone (3.4 mmol) were mixed well by grinding. The mixture was taken in a sealed vial and subjected to MW irradiation. After the reaction was complete, the product was purified by passing through a short silica gel column (eluant, hexane/EtOAc = 9:1). (b) In PEG-400: A well ground mixture of 1,2-diaminobenzene (0.37 g, 3.4 mmol), oximino ketone (3.4 mmol) and PEG-400 was taken in a sealed vial and irradiated with MW. After the reaction was over, the product was obtained as mentioned in the previous case. (c) In AcOH: The same amounts of reactants as mentioned in the previous cases were ground with 2-3 drops of AcOH, and the mixture was subjected to the same procedure as mentioned earlier. The one-pot reaction: Sodium nitrite (0.617 g, 8.9 mmol) in 1 mL of water was taken in a 25 mL flask and cooled to -15 °C. Ketone (7.5 mmol) in 1 mL of PEG-400 was added, followed by concd HCl (0.33 g) over 5 min. The mixture turned green. After the colour disappeared (about 45 min), 0.74 g (6.8 mmol) of 1,2-diaminobenzene was added. The mixture was transferred to a vial and subjected to MW irradiation (9 min). After the reaction was over, the product was added to 10 mL of water and worked up in the usual way using dichloromethane for extraction.
References:
Padmavathy;Nagendrappa, Gopalpur;Geetha [Tetrahedron Letters,2011,vol. 52,# 4,p. 544 - 547] Location in patent:experimental part
22027-53-8
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