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A method for synthesizing amides from aldehydes
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A technology for synthesizing amides and aldehydes, applied in the field of organic synthetic chemistry, to achieve the effect of low catalyst load and broad development prospects
Inactive Publication Date: 2016-12-28
NANJING UNIV OF SCI & TECH
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The disadvantage of the reaction is that it needs to be carried out at 160 ° C, and the reaction also generates by-products such as nitrile
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Embodiment 1
[0021] Example 1: 4-Chlorobenzamide
[0022] 4-chlorobenzamide
[0023]
[0024] Add 4-chlorobenzaldehyde (70.3mg, 0.5mmol), hydroxylaminehydrochloride (34.7mg, 0.5mmol), sodiumcarbonate (26.5mg, 0.25mmol) and water (1ml) into a 25ml Schlenk reaction flask successively, and react half Hours later, add [Cp*Ir(H 2 O) 3 ][OTf] 2 (5.1 mg, 0.0075 mmol, 1.5 mol%), the reaction mixture was reacted at 110° C. for 12 hours, cooled to room temperature, water was removed by rotary evaporation, and the target compound was obtained by column separation with a yield of 85%. 1 H NMR (500MHz, DMSO-d 6 )δ8.06 (br s, 1H, NH), 7.88 (d, J=8.4Hz, 2H, ArH), 7.52 (d, J=8.4Hz, 2H, ArH), 7.48 (br s, 1H, NH) ; 13 C NMR (125MHz, DMSO-d 6 )δ166.8, 136.1, 133.0, 129.4, 128.3.
Embodiment 2
[0025] Example 2: 3,4-dichlorobenzamide
[0026] 3.4-dichlorobenzamide
[0027]
[0028] 3,4-dichlorobenzaldehyde (87.5mg, 0.5mmol), hydroxylamine hydrochloride (34.7mg, 0.5mmol), sodiumcarbonate (26.5mg, 0.25mmol) and water (1ml) were successively added to a 25ml Schlenk reaction flask, After reacting at room temperature for half an hour, add [Cp*Ir(H 2 O) 3 ][OTf] 2 (5.1 mg, 0.0075 mmol, 1.5 mol%), the reaction mixture was reacted at 110° C. for 12 hours, cooled to room temperature, water was removed by rotary evaporation, and the target compound was obtained by column separation with a yield of 80%.
[0033] Add 4-bromobenzaldehyde (92.5mg, 0.5mmol), hydroxylamine hydrochloride (34.7mg, 0.5mmol), sodiumcarbonate (26.5mg, 0.25mmol) and water (1ml) into a 25ml Schlenk reaction flask successively, and react half Hours later, add [Cp*Ir(H 2 O) 3 ][OTf] 2 (10.2 mg, 0.0150 mmol, 3 mol%), the reaction mixture was reacted at 110° C. for 12 hours, cooled to room temperature, water was removed by rotary evaporation, and the target compound was obtained by column separation, yield: 65%. 1 H NMR (500MHz, DMSO-d 6 )δ8.06 (br s, 1H, NH), 7.81 (d, J=8.1Hz, 2H, ArH), 7.67 (d, J=8.1Hz, 2H, ArH), 7.48 (br s, 1H, NH) ; 13 C NMR (125MHz, DMSO-d 6 )δ166.9, 133.4, 131.2, 129.6, 125.0.
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Abstract
The invention discloses a method for synthesizing amides from aldehyde. The method comprises the following steps: adding aldehyde, hydroxylaminehydrochloride, alkali and water to a reaction vessel to react at room temperature for half an hour; adding a water-soluble iridium complex after aldehyde is completely transformed into oxime, cooling a reactant to the room temperature after the reaction mixture reacts at 80-120 DEG C for several hours, removing water through selective evaporation, and obtaining a target product through column separation. Compared with existing methods for synthesizing amides by generating oxime through one-pot reaction between aldehyde and hydroxylamine in water and then carrying out rearrangement, the method has the advantages that the used catalyst is low in load and does not contain phosphine ligands severely polluting the environment, so that the reaction can be carried out in the air, without nitrogen protection; therefore the reaction meets the green chemical requirements and has an extensive development prospect.
Description
technical field [0001] The invention belongs to the technical field of organic synthesischemistry, and in particular relates to a method for synthesizing amides from aldehydes. Background technique [0002] Amides are important functional groups of proteins and are also used as intermediates in the synthesis of fine chemicals, natural products and polymers, etc. The traditional method of synthesizing amides is to react carboxylic acid derivatives (such as acid chlorides, anhydrides and esters) with ammonia. Although widely used, the raw materials used in this method are highly toxic and corrosive to equipment. , the reaction releases a large amount of energy and produces a large amount of spent acid, and at the same time has poor adaptability to certain functional groups and low atom economy. The other is under the condition of strong acid and high temperature, through the isomerization of oxime, the Beckmann rearrangement reaction occurs to directly generate the target pr...
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