4-Amino-m-cresol → 3-Isobutyryl-4-(4-hydroxy-2-methylphenylamino)-8-methoxyquinoline

HRID 1885178Notes

Reaction equation

HRID 1885178 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])[CH:2]([CH3:4])[CH3:3].[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])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 100841433-Isobutyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 198802793-Isobutyryl-4-(4-hydroxy-2-methylphenylamino)-8-methoxyquinolineYield 55.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-isobutyryl-4-chloro-8-methoxyquinoline (1.32 g, 5 mmol) and 4-amino-3-methylphenol (0.62 g, 5 mmol) in dioxan (50 ml) was heated at reflux for 1 hour, then cooled and the solid filtered off. This was taken up in a hot mixture of ethanol and tributylamine, cooled, and the solid filtered off. Recrystallisation from ethanol gave 3-isobutyryl-4-(4-hydroxy-2-methylphenylamino)-8-methoxyquinoline (0.97 g, 55%), m.p. 243°-5°.

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. filtrationthe solid filtered off
  4. additionThis was taken up in a hot mixture of ethanol and tributylamine
  5. temperaturecooled
  6. filtrationthe solid filtered off
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-fb97076a68e74bfd99976f825edacbdc
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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