2447-93-0

Usage

InChI:InChI=1/C14H12ClNO/c1-10-6-8-11(9-7-10)16-14(17)12-4-2-3-5-13(12)15/h2-9H,1H3,(H,16,17)

Upstream product

• 609-65-4 o-chlorobenzoyl chloride 
• 106-49-0 p-toluidine 
• 118-91-2 ortho-chlorobenzoic acid 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 26118-14-9 o-chlorobenzoylformic acid 

Downstream Products

• 213454-29-6 N-(α,o-dichlorobenzylidene)aniline 
• 66087-54-5 2-Chlor-N,4'-dimethylbenzanilid 
• 878966-10-0 2-chloro-N-(2-fluoro-4-methylphenyl)benzamide 
• 33238-15-2 3-phenylmethylene-2-(4-methylphenyl)isoindole-1-one 
• 1384754-96-4 [(C₆H₄C(O)NC₆H₄-4-Me)Co(III)(Cl-ortho-C₆H₄C(O)NC₆H₄-4-Me)(trimethylphosphine)2] 
• 1384754-93-1 trans-[(C₆H₄C(O)NHC₆H₄-4-Me)Ni(II)(trimethylphosphine)2Cl] 
• 14959-59-2 C₂₈H₂₁NO 
• 14959-73-0 3,4-diphenyl-2-(p-tolyl)isoquinolin-1(2H)-one 
• 213454-64-9 ethyl ethyl-1,4-dihydro-2-methyl-4-(4'-methylphenyl)imino-3-quinolinecarboxylate 

Relevant academic research and scientific papers

Catalyst-Free Singlet Oxygen-Promoted Decarboxylative Amidation of α-Keto Acids with Free Amines

A novel catalyst-free decarboxylative amidation of α-keto acids with amines under mild conditions has been developed. Advantages of the new protocol include avoidance of metal catalysts and high levels of functional group tolerance. In addition, the reaction can be scaled up and shows high chemoselectivity. Preliminary mechanistic studies suggest that singlet oxygen, generated from oxygen under irradiation, is the key promoter for this catalyst-free transformation.

Direct arylation under catalysis of an oxime-derived palladacycle: Search for a phosphane-free method

A phosphane-free method for the direct arylation of benzothiazole by employing oxime-derived palladacycle 1 as a catalyst was developed. The new catalyst system can be used for 2-arylations by using aryl bromides and iodides. In addition, this method is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well aschloroamides, to achieve a rapid synthesis of benzo[c]phenanthridine alkaloids. Direct arylation reactions under catalysis of an oxime-derived palladacycle were investigated. This phosphane-free method is applicable for the 2-arylation of benzothiazole and is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well as chloroamides, to achieve rapid synthesis of benzo[c]phenanthridine alkaloids. Copyright

Efficient and convenient deprotection of thiocarbonyl to carbonyl compounds using 3-carboxypyridinium and 2,2′-bipyridinium chlorochromates in solution, dry media, and under microwave irradiation

A synthetic utility of 3-carboxypyridinium (CPCC) and 2,2′- bipyridinium (BPCC) chlorochromates in deprotection reactions is reported. Different types of thioamides, thioureas, thiono esters, and thioketones are deprotected to their corresponding carbonyl compounds with these reagents in good to excellent yields. The reactions were carried out in solution, under solvent-free conditions, and under microwave irradiation. The results show that with both reagents the rates of the reactions and the yields are usually highest under microwave irradiation. Springer-Verlag 2003.

Bismuth(III) nitrate pentahydrate: A convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds

A variety of thioamides and thioureas are rapidly transformed to their oxo derivatives with Bi(NO3)3·5H2O in excellent yields. However, thiono esters and thioketones are converted to their corresponding carbonyl compounds in only poor yields. Bi(NO3)3·5H2O is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the selective deprotection of thioamides and thioureas in the presence of thiono esters and thioketones make this method an attractive alternative to the existing routes for deprotection of thiocarbonyl compounds.

Selective conversion of thioamides and thioureas to their oxygen analogues using quinolinium fluorochromate

The synthetic utility of quinolinium fluorochromate (QFC) in deprotection of thiocarbonyl compounds is reported. A variety of primary and secondary thioamides and thioureas are converted to their oxo derivatives in high yields. However, tertiary thioamides afford their amides in relatively poor yields. Selective deprotection of thioamides and thioureas in the presence of thionoesters and thioketones is noteworthy advantage of this method.

A facile and convenient method for deprotection of thiocarbonyls to their carbonyl compounds using oxone under aprotic and nonaqueous conditions

The reaction of oxone as an inexpensive, stable, and commercially available reagent with thiocarbonyl compounds in refluxing acetonitrile has been studied. Primary, secondary, and tertiary thioamides and thioureas are converted to their oxo analogues efficiently. Thiono esters also are transformed to their corresponding esters, while thioketones remained intact under these conditions.

Convenient transformation of thiocarbonyl to carbonyl group using benzyltriphenylphosphonium and n-butyltriphenylphosphonium peroxodisulfates

Benzyltriphenylphosphonium and n-butyltriphenylphosphonium peroxodisulfates are stable and easily prepared oxidising agents. These reagents are able to convert different thioamides and thioureas to their oxygen analogues in good to excellent yields. Thiono esters are also transformed to esters in high yields. Thioketones such as thiobenzophenone and thiofluorenone are converted to their ketones in high yields while, 4-nitrothiobenzophenone, 2-aminothiobenzophenone and 4-chlorothiobenzophenone remained intact in the reaction mixture.

A convenient and inexpensive method for conversion of thiocarbonyl compounds to their oxo derivatives using oxone under solvent-free conditions

A series of thioamides, thioureas and thioesters are transformed to their corresponding carbonyl compounds in good to excellent yields with oxone under solid phase conditions, while thioketones remained unchanged under these conditions.

Zeolite-HY : A selective and efficient catalyst for the synthesis of amides under microwave irradiations

An efficient and selective method for the conversion of various acids into their corresponding amides in the presence of zeolite under microwave irradiation is described. The reaction proceeds efficiently at ambient pressure in high yields.