Dimethylformamide → Sch 37224

반응식

[H-].[Na+].[CH3:3][N:4]([CH3:7])[CH:5]=[O:6].C(O[C:11](=[O:18])[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)C.C1(C)[C:20](C)=[CH:21][CH:22]=[CH:23][CH:24]=1>>[OH:18][C:11]1[C:17]2[C:3](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]([C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:5](=[O:6])[C:12]=1[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 7237O-Xylene

HCID 24758Sodium hydride2회

HCID 2109961-Pyrrolidineacetic acid, ethyl ester2회

생성물 1

HCID 54680204Sch 37224수율 60%

반응 조건

온도: 0 °C

실험 절차

To a solution of 1.5 g (6.5 mM) 2-anilinonicotinic acid, methylester, in dry xylenes at room temperature is added 0.69 g (14.54 M) of sodium hydride (NaH) (50 percent (%) oil emulsion) followed by addition of a small amount of N,N-dimethylformamide (DMF). The reaction mixture is heated to a temperature ranging between 85-95 degrees Centigrade (°C.) and 1.05 milliliters (mL) (6.5 mM) of ethyl-1-pyrrolidineacetate in xylene is slowly added over a period of 10 minutes. The reaction mixture is heated for 1 to 3 hours prior to the addition of aliquots of 0.32 g NaH followed by 1.05 mL of ethyl-1-pyrrolidineacetate as described above (total 3 aliquots). Following addition of the aliquots, the reaction mixture is cooled to 0° C., quenched with a slow addition of glacial acetic acid, and then water is added. The product is filtered and washed with water, acetone, methylene chloride, and acetone. The solid then obtained is dried in vacuo to give 1.20 g (60% yield) of title compound, a white solid.