53012-96-7

Basic information

• Product Name: 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile
• Synonyms: 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile
• CAS NO: 53012-96-7
• Molecular Weight: 207.659
• Mol File: 53012-96-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile(53012-96-7)
• EPA Substance Registry System: 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile(53012-96-7)

Safety Data

• Hazardous Substances Data: 53012-96-7(Hazardous Substances Data)

Upstream product

• 174869-06-8 α-(2-cyano-1-methylethyl)-4,4'-dichlorobenzoin 
• 3457-46-3 4,4'-dichlorobenzil 
• 4786-20-3 but-2-enenitrile 
• 104-88-1 4-chlorobenzaldehyde 
• 773837-37-9 sodium cyanide 
• 4786-20-3 crotononitrile 

Downstream Products

• 118428-37-8 pimobendan 
• 85634-10-2 5-methyl-6-(3'-amino-4'ethylamino-phenyl)-4,5-dihydro-3(2H)-pyridazinone 
• 85634-12-4 5-methyl-6-(3'-amino-4'-isopropylamino-phenyl)-4,5-dihydro-3(2H)-pyridazinone 
• 85634-04-4 5-methyl-6-(1'-benzyl-benzotriazol-5'-yl)-4,5-dihydro-3(2H)-pyridazinone 

Relevant articles and documents

Synthesis of novel pyridazinonylbenzotriazoles

4-Chlorobenzaldehyde (1) was reacted with crotononitrile (2) in the presence of sodium cyanide yielding 4-(4-chlorophenyl)-3-methyl- 4-oxobutyronitrile (3) which on refluxing with concentrated HCl gave 4-(4-chlorophenyl)-3-methyl-4-oxobutyric acid (4). The latter, on treatment with fuming nitric acid, yielded 4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid (5), which on treatment with hydrazine hydrate gave 6-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazine-3-one (6). Azidation and reduction of 6 with sodium azide gave the amino derivative 7 which on reductive alkylation gave 10(a-i) followed by reduction with commercially available sodium hydrogen sulphide solution gave the substituted diamine derivative 11(a-i). The compound 7 directly undergoes reduction with sodium hydrogen sulphide yielding (8). Finally, 8 and 11(a-i) was converted into the target compounds by diazotized-cyclization with sodium nitrite giving pyridazinonylbenzotriazoles 9 and 12(a-i).

CRYSTALLINE PIMOBENDAN, PROCESS FOR THE PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION AND USE

The invention relates to a pharmaceutical composition containing pimobendan as an active ingredient. The invention also relates to a crystalline form of pimobendan, as well as to a combination of said crystalline form with at least one other therapeutically active ingredient. Moreover, the invention relates to uses of said crystalline form, as well as to a pharmaceutical composition containing it. Finally, the invention relates to a process for preparing a crystalline form of pimobendan.

Synthesis of ketones by retro-benzoin condensation catalyzed by potassium cyanide

The treatment of 2-benzyl-1,2-diphenyl-2-hydroxyethanone (3a, benzylbenzoin) with potassium cyanide in DMF gave deoxybenzoin (4a). The formation of deoxybenzoin (4a) proceeds through retro-benzoin condensation by catalytic action of cyanide ion. Similarly, retro-benzoin condensation applied to several substituted benzoins 3 resulted in the formation of the corresponding ketones 4 in excellent yields.