Electric Literature of 36865-41-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 36865-41-5 as follows.
A mixture of 327 mg (2.00 mmole) OF 7-HYDROXY-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (prepared as detailed in WO 01/77100 utilizing 3-aminophenol in place of 4-aminophenol) and 415 mg (3.0 mmole) of potassium carbonate in 8 ML of CH3CN was heated at reflux for 22 hr. After cooling to room temperature, the mixture was diluted with EtOAc, filtered through celite, and concentrated. Purification by flash column chromatography (SiO2, 20% EtOAc/hexanes gradient to 70% ETOAC/HEXANES) GAVE 380 mg (75%) of 7-BENZYLOXY-3, 4-DIHYDRO-1H-QUINOLIN- 2-one as a white solid. MS : M/Z 254.1 (M+1) 7-BENZYLOXY-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (379 mg, 1.50 mmole) was dissolved in 8 ML of anhydrous DMF under a N2 atmosphere and cooled in an ice bath. NaH (57 mg, 2.24 mmole) was added in a single portion, and the resulting gray suspension was stirred at 0 C for 10 min. 3-BROMO-L-METHOXYPROPANE (275 mg, 1. 8 mmole) was added, and the reaction mixture was stirred at room temperature for 3 hr. Excess hydride was quenched by the addition of a large excess of H2O, and the aqueous layer was extracted with EtOAc (3x). The combined organic layers were washed with H20 (2X) and brine, dried over MGS04, filtered, and concentrated. Purification by flash column chromatography (SIO2, 10% EtOAc/hexanes gradient to 40% ETOAC/HEXANES) provided 382 mg (78%) of 7-BENZYLOXY-L- (3-METHOXYPROPYL)- 3, 4-DIHYDRO-LH-QUINOLIN-2-ONE as a clear viscous oil. MS : M/Z 326.1 (M+1) 7-BENZYLOXY-1- (3-METHOXYPROPYL)-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (355 mg, 1.09 mmole) was dissolved in 50 mL of MEOH and hydrogenated over 0.1 g of 20% Pd/C at 50 psi for 16 hr. The catalyst was removed by filtration through celite, and the solution was concentrated to dryness to afford 259 mg (100%) of 7-HYDROXY-L- (3-METHOXYPROPYL)-3, 4- DIHYDRO-LH-QUINOLIN-2-ONE as a light brown viscous oil which was used without further purification. MS: NIEZ 236. 1 (M+1)
According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/89915; (2004); A1;,
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