Hydrochloric Acid → HCID 66913734, compound

HRID 2104736Notes

Reaction equation

HRID 2104736 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]#[N:23])[CH:5]=[CH:6][CH:7]=1.[OH:24]O.[OH-].[Na+].Cl>C(O)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:19])[F:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([NH2:23])=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 66913696HCID 66913696, compound

Product 1

HCID 66913734HCID 66913734, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-(3-aminophenyl)-8-(trifluoromethyl)quinoline-3-carbonitrile (0.30 g, 0.96 mmol), 30% hydrogen peroxide (5 mL), NaOH (0.5 g, 12 mmol) and ethanol (15 mL) was heated to ˜40° C. for 3 hours. The pH of the solution was adjusted to ˜6 by diluted HCl. The reaction mixture was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded onto silica gel and chromatographed with hexanes:ethyl acetate (50% to 100%) to afford 0.13 g of the title compound as an off-white solid. MS (ESI) m/z 332;

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe organic phases were concentrated
  6. customchromatographed with hexanes

Sources & evidence

ORD record
ord-0047317f0d214c4a9bc8a3aa43f5868b
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

Loading…