Diethyl (ethoxymethylene)malonate → Diethyl 2-(((3-fluoro-4,5-dimethoxyphenyl)amino)methylene)malonate

HRID 525933Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10])[NH2:5].C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To the suspension of 3-fluoro-4,5-dimethoxyaniline (73 g, 426 mmol) in Ethanol (100 mL) was added diethyl 2-(ethoxymethylene)malonate (85 mL, 426 mmol), and the resulting mixture was heated at 80° C. for 1 h. LCMS indicated completion of the reaction. The mixture was concentrated in vacuo to remove ethanol, and the residue was washed with hexane to afford diethyl 2-(((3-fluoro-4,5-dimethoxyphenyl)amino)methylene)malonate (142 g, 416 mmol, 98% yield) as a yellow solid. LCMS: (M+H)+: 342.1.

Workup

customcompletion of the reaction
concentrationThe mixture was concentrated in vacuo
customto remove ethanol
washthe residue was washed with hexane

Sources & evidence

ORD record: ord-105776c3b46443a2a7ea413fb9be6409
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340556B2

Reaction notes

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