4-CHLORO-2-METHYLBENZALDEHYDE

To a solution of commercial General procedure: Compound 1 (0.4 mol), N-bromosuccinimide (NBS) (0.48 mol, 85.4 mg), and Pd(OAc)2(10 mol%, 8.9 mg), 2-Amino-5-chlorobenzotrifluoride (20 mol%, 15.6 mg) were mixed withDCE (2.5 mL) and TFA (0.5 mL) solvent. The reaction mixture was stirred 24 h at 60 C. Aftercompletion of the reaction, the solution was concentrated in vacuo and purified by columnchromatography on silica gel using PE/DCM/EtOAc as eluent to give the desired product.General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.2 mmol), glycine (0.2 mmol, 15.0 mg), Pd(OAc)2 (0.02 mmol, 4.5 mg), AgTFA (0.6 mmol, 132.8 mg) and 2 (0.3 mmol) under air. After addition of AcOH (2.0 mL) as solvent, TfOH (0.2 mmol, 30.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using petroleum ether as the eluent to afford the desired products.General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.2 mmol), glycine (0.2 mmol, 15.0 mg), Pd(OAc)2 (0.02 mmol, 4.5 mg), AgTFA (0.6 mmol, 132.8 mg) and 2 (0.3 mmol) under air. After addition of AcOH (2.0 mL) as solvent, TfOH (0.2 mmol, 30.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using petroleum ether as the eluent to afford the desired products.General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.2 mmol), glycine (0.2 mmol, 15.0 mg), Pd(OAc)2 (0.02 mmol, 4.5 mg), AgTFA (0.6 mmol, 132.8 mg) and 2 (0.3 mmol) under air. After addition of AcOH (2.0 mL) as solvent, TfOH (0.2 mmol, 30.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using petroleum ether as the eluent to afford the desired products.General procedure: To a solution of biphenyl carboxaldehyde 1d (0.1 g, 0.54 mmol) in ethanol (1.5 mL) was added N, N-dimethyl barbituric acid, 4 (0.1 g, 0.64 mmol), ninhydrin, 2 (0.1 g, 1.0 mmol), sarcosine, 3 (57 mg, 0.64 mmol) and magnesium silicate catalyst (10 mol%) at room temperature. The reaction mass was irradiated by microwave irradiations in a Microwave Vials 0.2-0.5mL of Biotage Initiator at 120 C, 300 W, 2 bar reactionpressure for 90 min and until the completion of starting material. The title compound was precipitated as yellow solid on standing the reaction mass. Then it was filtered and washed with cold methanol to remove polar impurities. The compound was further recrystallized using dichloromethane:methanol: tetrahydrofuran (3:1:1) to get 88% yield as colorless prisms.

Molecular Weight:154.59
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:154.0185425
Monoisotopic Mass:154.0185425
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes