Sodium Hydroxide → HCID 118075914, compound

HRID 1051567Notes

Reaction equation

HRID 1051567 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[OH-].[Na+]>[Pd].CO>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:2][CH:3]=[CH:4][C:5]=2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118075381HCID 118075381, compound

Product 1

HCID 118075914HCID 118075914, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A Parr bottle was charged with 8-chloro-2-methyl-5-phenoxyquinoline (0.93 g, 3.45 mmol), methanol (20 mL), and 3 M aqueous sodium hydroxide solution (3.79 mL, 11.38 mmol). The bottle was flushed with nitrogen, and 10% palladium on carbon (0.5 g, 0.470 mmol) was added. The mixture was then shaken under an atmosphere of hydrogen (30 psig). After 4.5 h, the mixture was filtered through a pad of Celite. The bottle and filter pad were rinsed with methanol. The filtrate was concentrated under reduced pressure. The residue was then partitioned between ethyl acetate and 5% aqueous sodium chloride solution (25 mL). The layers were separated, and the organic layer washed again with 5% aqueous sodium chloride solution (25 mL). The aqueous washes were extracted once with ethyl acetate, and the combined extracts were concentrated to afford crude 2-methyl-5-phenoxyquinoline (0.82 g, 101%) as a pale yellow-orange syrup which was used without further purification. MS (ESI, pos. ion) m/z 236 [M+1].

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered through a pad of Celite
  3. filtrationThe bottle and filter pad
  4. washwere rinsed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was then partitioned between ethyl acetate and 5% aqueous sodium chloride solution (25 mL)
  7. customThe layers were separated
  8. washthe organic layer washed again with 5% aqueous sodium chloride solution (25 mL)
  9. extractionThe aqueous washes were extracted once with ethyl acetate
  10. concentrationthe combined extracts were concentrated

Sources & evidence

ORD record
ord-71bef4dad1d04c13bfe205c6af9e8dd7
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

Loading…