246136-27-6

Upstream product

• 1719-99-9 2-bromo-4-chloro butyryl bromide 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 167834-20-0 4-(3-Amino-2-oxo-pyrrolidin-1-yl)-benzonitrile 
• 213978-36-0 3-bromo-1-(4-cyanophenyl)pyrrolidin-2-one 

Relevant academic research and scientific papers

Kinetics and mechanism of formation and decomposition of substituted 1-phenylpyrrolidin-2-ones in basic medium

A study of chemical behaviour of substituted 4-chloro-N-phenylbutanamides in aqueous solutions of sodium hydroxide showed that the substrate first undergoes ring closure to give substituted 1-phenylpyrrolidin-2-ones, which are subsequently hydrolysed to substitution derivatives of sodium 4-amino-N-phenylbutanoates. Kinetic measurements provided the values of dissociation constants pKa and cyclization rate constants kc in water at 25°C for 2-bromo-4-chloro-N-(4-nitrophenyl)butanamide [pKa = 11.64 ± 0.01; kc = (1.94 ± 0.03) × 10-2 s-1], 4-chloro-N-(4-nitrophenyl)butanamide [pKa = 13.35 ± 0.02; kc = (1.60 ± 0.02) × 10-2 s-1 and 4-chloro-2-methyl-N-(4-nitrophenyl)butanamide [pKa = 13.55 ± 0.03; kc = (7.61 ± 0.11) × 10-2 s-1]. The pKa and kc values of individual derivatives differ depending on the substitution at the α-position of the butanamide skeleton. In methanolic sodium methoxide solutions, the course of ring closure of 2-bromo-4-chloro-N-(4-nitrophenyl)butanamide is of similar nature but slower [K = 60.10 ± 0.08 and kc = (6.52 ± 0.05) × 10-3 s-1]. The subsequent hydrolyses of substituted 1-phenylpyrrolidin-2-ones to substituted 4-aminobutanoic acids also have different courses with different derivatives and depend on the substituents in the aromatic and/or heterocyclic moiety. The rate-limiting step of hydrolysis of 1-(4-nitrophenyl)pyrrolidin-2-one consists of the non-catalysed decomposition of the tetrahedral intermediate. In the case of 3-bromo-1-(4-nitrophenyl)pyrrolidin-2-one at sodium hydroxide concentrations below 0.1 mol 1-1, the rate-limiting step is the second reaction pathway, i.e. the hydroxide ion-catalysed decomposition of the tetrahedral intermediate. At sodium hydroxide concentrations above 0.1 mol 1-1], the rate-limiting step shifts to formation of the tetrahedral intermediate. This formation of the intermediate is 140 times slower than its hydroxide ion-catalysed decomposition [k3/k-1 = (1.40 ± 0.04) × 102 1 mol-1]. Introduction of a 3-bromo substituent into 1-(4-nitrophenyl)pyrrolidin-2-one results in acceleration of all the reaction steps of hydrolysis and increases the acidity of the intermediate. Copyright

Process for the preparation of a 2-oxopyrrolidine compound

A process for producing a lactam of the formula STR1 wherein 2-bromo-4 chloro butyryl bromide or 2,4-dibromo butyryl bromide is coupled with 4-aminobenzonitrile to produce 4-(2,4-bromobutyrylamino)-benzonitrile, which is combined with sodium hydroxide, po

An efficient asymmetric synthesis of (3S)-3-amino-1-(4-cyanophenyl)-2- oxopyrrolidine hydrochloride salt

Reaction of 4-aminobenzonitrile with 2-bromo-4-chlorobutyryl bromide in the presence of sodium phosphate followed by treatment of the coupled product with sodium hydroxide followed by ammonium hydroxide in acetonitrile yielded the title compound as the ra