4-Amino-3,5-dimethylphenol → 3-Butyryl-4-(4-hydroxy-2,6-dimethylphenylamino)-8-methoxyquinoline

HRID 1885164Notes

Reaction equation

HRID 1885164 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1Cl)=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])(=[O:15])[CH2:12][CH2:13][CH3:14]>O1CCOCC1>[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1[NH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10])=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])(=[O:15])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 765434-Amino-3,5-dimethylphenolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 103841703-Butyryl-4-(4-hydroxy-2,6-dimethylphenylamino)-8-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Amino-3,5-dimethylphenol (1.8 g, 1.3 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (2.6 g, 10 mmol) were heated together under reflux in 1,4-dioxan (50 ml) for 2 hours. The solvent was evaporated and the residue dissolved in dichloromethane, washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to a yellow solid which on recrystallisation from ethanol, followed by methanol, afforded 3-butyryl-4-(4-hydroxy-2,6-dimethylphenylamino)-8-methoxyquinoline as yellow crystals, m.p. 247°-8°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water, sodium hydrogen carbonate solution and brine
  4. customdried
  5. customevaporated to a yellow solid which on recrystallisation from ethanol

Sources & evidence

ORD record
ord-a96a22f48e5b4c10974331c8c22880d5
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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