Hydrochloric Acid → HCID 66914149, compound

HRID 2104593Notes

Reaction equation

HRID 2104593 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[C:27]([F:30])([F:29])[F:28])=[O:10])=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.Cl>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[C:27]([F:30])([F:28])[F:29])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 66913824HCID 66913824, compound

Product 1

HCID 66914149HCID 66914149, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Methoxyphenyl)[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (0.174 g) and pyridine hydrochloride are heated at 200° C. for 2 h and then cooled. The resulting solid is taken into methylene chloride and 2N aq HCl. The layers are separated, the aqueous layer is extracted again, and the combined organics are washed with saturated sodium bicarbonate and dried over MgSO4. The residue is chromatographed eluting with 25:75 ethyl acetate:hexane to afford the title compound as a white solid (0.132 g). MS (ES) m/z 392.1; HRMS: calcd for C23H14F3NO2—H, 392.08984; found (ESI, [M−H]−), 392.0883.

Workup

  1. temperaturecooled
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted again
  4. washthe combined organics are washed with saturated sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. customThe residue is chromatographed
  7. washeluting with 25:75 ethyl acetate

Sources & evidence

ORD record
ord-9bd55d1dcc7f466497549880c8797abf
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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