HCID 178471905, compound → HCID 178458757, compound

HRID 2271526Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]([C:16](=[O:19])[CH2:17][CH3:18])[C:11]([O:13]CC)=O)=[CH:4][CH:3]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[CH:9][C:10]([C:16](=[O:19])[CH2:17][CH3:18])=[C:11]2[OH:13]

Participants

Conditions

Temperature: 250 °C

Procedure

Dowtherm A (200 mL) was heated to 240° C. Ethyl 2-(((4-bromophenyl)amino) methylene)-3-oxopentanoate (25.1 g, 77 mmol) was added portionwise. The reaction was then heated to 250° C. and stirred for 1.25 h. The reaction mixture was slowly cooled to room temperature and a precipitate formed. The suspension was diluted with hexanes (500 mL) and filtered to afford the desired product (15.9 g, 73%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 12.64 (br s, 1H), 8.56 (s, 1H), 8.30 (d, J=2.3 Hz, 1H), 7.88 (dd, J=8.8, 2.4 Hz, 1H), 7.61 (d, J=8.8 Hz, 1H), 3.10 (q, J=7.2 Hz, 2H), 1.05 (t, J=7.2 Hz, 3H).

Workup

temperatureThe reaction mixture was slowly cooled to room temperature
customa precipitate formed
filtrationfiltered

Sources & evidence

ORD record: ord-be601274015c45c18be6014b1ce0f839
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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