Ethylene Glycol → 3-Benzyl-4-phenyl-8-(trifluoromethyl)quinoline

HRID 2104489Notes

Reaction equation

[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)CO.O.NN.[OH-].[K+]>O>[CH2:7]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:25]([F:28])([F:26])[F:27])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (Example 1, 0.244 g, 0.65 mmol) was taken into ethylene glycol (5 mL) along with hydrazine hydrate (0.3 mL) and heated at 120° C. for 2 hours. Next, a few pellets of KOH were added and reaction was heated at 180° C. for 4 hours. The reaction was allowed to cool to room temperature, where water was added and the mixture was extracted with ether and concentrated. The resulting material was purified via column chromatography using 5% ethyl acetate in hexane as the eluent to produce 0.128 g of desired product. MS (ESI) m/z 364 ([M+H]+); 1H NMR (CDCl3) δ 9.01 (s, 1H), 8.02 (d, J=7.2 Hz, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.51 (m, 3H), 7.44 (m, 1H), 7.20 (m, 5H), 6.97 (m, 2H), 3.98 (s, 2H).

Workup

customreaction
temperaturewas heated at 180° C. for 4 hours
temperatureto cool to room temperature
extractionthe mixture was extracted with ether
concentrationconcentrated
customThe resulting material was purified via column chromatography

Sources & evidence

ORD record: ord-2f9bf6c7140f4b8695e533d5f20c5f82
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576215B2

Reaction notes

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