4-Amino-m-cresol → HCID 11725437, compound

HRID 1885163Notes

Reaction equation

HRID 1885163 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=1[CH3:27]>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=1[CH3:27])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 11725437HCID 11725437, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methoxyquinoline (3.95 g, 15 mmol), 4-amino-3-methylphenol (2.46 g, 20 mmol) and 1,4-dioxan (15 ml) were warmed briefly to reflux, then the solid filtered off and washed with ethyl acetate. Conversion to free base and recrystallisation from ethanol gave 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-8-methoxyquinoline (1.79 g, 34%), m.p. 252°-253°.

Workup

  1. temperatureto reflux
  2. filtrationthe solid filtered off
  3. washwashed with ethyl acetate
  4. customConversion to free base and recrystallisation from ethanol

Sources & evidence

ORD record
ord-5e2f174422da4ec2988f1732e53a7e6c
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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