Sodium ethoxide → ethyl 2-(4-fluorophenyl)-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907960Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH:6]=[N:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][O:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[CH3:20][N:21]1[C:25]([CH:26]=O)=[N:24][CH:23]=[N:22]1.[O-:28][CH2:29][CH3:30].[Na+]>C(OCC)(=O)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]2[CH:26]([C:25]3[N:21]([CH3:20])[N:22]=[CH:23][N:24]=3)[C:29](=[O:28])[C:30]3[C:13]([C:12]([O:11][CH2:10][CH3:9])=[O:17])=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7]2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-(4-fluorobenzylideneamino) isobenzofuran-1(3H)-one (5.0 g, 19.6 mmol) and 1-methyl-1H-1,2,4-triazole-5-carbaldehyde (2.8 g, 25.5 mmol) in ethyl propionate (310 mL) was added sodium ethoxide (1.26 g, 54.9 mmol) at room temperature under nitrogen. The mixture was stirred at 55° C. for 2 hr. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (150 mL×4) and concentrated the extracts. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 1.5:1). A solid product was obtained (2.4 g, yield 31%). LC-MS (ESI) m/z: 395 (M+1)+.

Workup

customThen the resulting mixture was evaporated under reduced pressure
extractionextracted with ethyl acetate (150 mL×4)
concentrationconcentrated the extracts
customThe crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 1.5:1)
customA solid product was obtained (2.4 g, yield 31%)

Sources & evidence

ORD record: ord-90d780c028a24a739504357a97705c90
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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