Cyclopropylamine → ethyl 3-(cyclopropylamino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)prop-2-enoate

HRID 2073816Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 9.0 g (27.0 mmol) of ethyl 2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)-3-ethoxyacrylate in 30 ml of absolute ethanol at 5° C. was added 1.68 g (29.4 mmol) of cyclopropylamine. The mixture was stirred at 5° C. for 1.5 hours and at room temperature for 2.5 hours. The solution was concentrated to an oil which was triturated with hexane to give a tan solid. The crude product was recrystallized from hexane to give 9.07 g of the title compound, mp 72°-74° C.

Workup

concentrationThe solution was concentrated to an oil which
customwas triturated with hexane
customto give a tan solid
customThe crude product was recrystallized from hexane

Sources & evidence

ORD record: ord-3ba8195a7c444845817d801c32bfaa60
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04920120

Reaction notes

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