Hydrochloric Acid → HCID 66913506, compound

HRID 2104612Notes

Reaction equation

HRID 2104612 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[C:10]1[C:19]2[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.N1C=CC=CC=1.Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:10]1[C:19]2[C:14](=[C:15]([C:20]([F:23])([F:21])[F:22])[CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 66913753HCID 66913753, compound

Product 1

HCID 66913506HCID 66913506, compoundYield 65%

Conditions

Temperature
200 °C

Procedure

4-(2-Fluoro-5-methoxyphenyl)-3-phenyl-8-(trifluoromethyl)quinoline (0.230 g, 0.578 mmol) was combined with pyridine-HCl (50 g) and raised to 200° C. in and oil bath for 2 hours. Upon cooling to a solid waxy solid, 2N HCl was added and the solid dissolved, poured into a separatory funnel and extracted with ethyl acetate. The combined organic phases were washed with sat. NaHCO3, water, brine, and dried with magnesium sulfate to afford 0.142 g (65%) of the title compound as a tan solid: mp 85° C.; Calcd. mass for C22H13NF4O 383 found by MS (ES) m/z 393.9.

Workup

  1. additionwas added
  2. dissolutionthe solid dissolved
  3. additionpoured into a separatory funnel
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with sat. NaHCO3, water, brine
  6. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-fc2abedeb0a447dc8f5eecddec24b2cd
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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