Acetone → 8,9-Diethoxy-1,2,3,4-tetrahydro-3-(2-morpholinoethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

반응식

[OH:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]2[C:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:11][C:10]=3[C:23](=[O:25])[O:24][C:4]=2[CH:3]=1.[CH2:26](OS(OCC)(=O)=O)[CH3:27].C([O-])([O-])=O.[K+].[K+].[CH3:41][C:42](C)=O>>[CH2:26]([O:1][C:2]1[C:7]([O:8][CH2:41][CH3:42])=[CH:6][C:5]2[C:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[CH2:11][C:10]=3[C:23](=[O:25])[O:24][C:4]=2[CH:3]=1)[CH3:27]

참가 물질

반응물 4

HCID 180Acetone

HCID 6163Diethyl Sulfate

HCID 11430Potassium Carbonate

HCID 214471671,2,3,4-tetrahydro-8,9-dihydroxy-3-(2-morpholinoethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

생성물 1

HCID 214471688,9-Diethoxy-1,2,3,4-tetrahydro-3-(2-morpholinoethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

실험 절차

A mixture of 0.01 m of 1,2,3,4-tetrahydro-8,9-dihydroxy-3-(2-morpholinoethyl)-5H-[1]benzopyrano[3,4-c]-pyridin-5-one, 0.022 m of diethylsulfate, and 0.1 m of K2CO3 in 500 ml of acetone was refluxed for 18 hr, filtered hot and evaporated. Residue was dissolved in CHCl3 and washed with 3% NaOH soln. CHCl3 soluble material was crystallized from MeOH containing an excess of HCl gas affording 1 g of product; mp 240°-260° C.