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

HRID 525887Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-fluoro-3,4-dimethoxyaniline (39 g, 228 mmol) in Ethanol (200 mL) was added diethyl 2-(ethoxymethylene)malonate (45.7 mL, 228 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 then washed with hexane to afford diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonate (72 g, 211 mmol, 93% yield) as a brown solid. LCMS (M+H)+: 342.1.

Workup

customcompletion of the reaction
concentrationThe mixture was concentrated in vacuo
customto remove ethanol
washwashed with hexane

Sources & evidence

ORD record: ord-cae3b62c34a5478396acca5ee3e49798
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340556B2

Reaction notes

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