(2E)-3-ethoxy-N-(4-trifluoromethylphenyl)prop-2-enamide → 6-(Trifluoromethyl)quinolin-2(1H)-one

HRID 1772210Notes

Reaction equation

C(O/[CH:4]=[CH:5]/[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:7])C>S(=O)(=O)(O)O>[F:18][C:15]([F:16])([F:17])[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:6](=[O:7])[CH:5]=[CH:4]2

Participants

Conditions

Temperature: 0 °C

Procedure

(2E)-3-ethoxy-N-(4-trifluoromethylphenyl)prop-2-enamide (3.44 g, 16.8 mmol) was added in several batches to sulfuric acid (20 ml) at 0° C. and then stirred for 2 hours at 0° C. The resulting mixture was quenched with ice-water (100 ml). The product was precipitated from water and collected by filtration to afford 6-(trifluoromethyl)-1,2-dihydroquinolin-2-one as a yellow solid (2.0 g, 56%). (ES, m/z): [M+H]+ 214. 1H NMR (300 MHz, DMSO): δ 8.14 (s, 1H), 8.03 (d, J=9.6 Hz, 1H), 7.80-7.83 (m, 1H), 7.45 (d, J=8.4 Hz, 1H), 6.61-6.65 (t, J=9.6 Hz, 1H).

Workup

customThe resulting mixture was quenched with ice-water (100 ml)
customThe product was precipitated from water
filtrationcollected by filtration

Sources & evidence

ORD record: ord-7864afaebd5d4b3f9a1db4a7a342e9e5
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249102B2

Reaction notes

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