Phenol → HCID 70257067, compound

HRID 366387Notes

Reaction equation

HRID 366387 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=CC=C[CH:8]=2)[N:3]=1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[OH-].[Na+]>[C:13]1([CH2:12][N:19]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:4]([NH2:3])=[C:9]3[CH2:8][CH2:2][CH2:11][CH:10]23)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 7504BenzylamineHCID 119282-Chloroquinoline

Product 1

HCID 70257067HCID 70257067, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Chloroquinoline derivative (Example 9(C)) (2.0 g, 9.8 mmol), benzylamine (1.2 g, 11.2 mmol) and phenol (4.0 g, 42.6 mmol) were heated at 180° C. for 3 hours. After cooling, 5M sodium hydroxide (50 cm3) was added and the organic components were extracted into dichloromethane, dried (Na2SO4), filtered and the solvent was evaporated. Any remaining volatiles were removed by distillation and the residue was dissolved in hot ethanol, decolorised (charcoal) and recrystallised to give an off-white powder.

Workup

  1. temperatureAfter cooling
  2. extractionthe organic components were extracted into dichloromethane
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customAny remaining volatiles were removed by distillation
  7. dissolutionthe residue was dissolved in hot ethanol
  8. customrecrystallised
  9. customto give an off-white powder

Sources & evidence

ORD record
ord-51b4edcc64784e84bca31006c60e2422
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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