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

HRID 2104489
Notes
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Reaction equation

HRID 2104489 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11360909Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone

Product 1

HCID 114171673-Benzyl-4-phenyl-8-(trifluoromethyl)quinolineYield 54.2%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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

  1. customreaction
  2. temperaturewas heated at 180° C. for 4 hours
  3. temperatureto cool to room temperature
  4. extractionthe mixture was extracted with ether
  5. concentrationconcentrated
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes