4-Amino-m-cresol → HCID 19880286, compound

HRID 1885194Notes

Reaction equation

HRID 1885194 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([O:17]C(=O)C1C=CC=CC=1)=[CH:11][C:10]=2[O:26][CH3:27])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:28][C:29]1[C:30]([CH3:36])=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=1[CH3:36])=[CH:13][C:12]([OH:17])=[CH:11][C:10]=2[O:26][CH3:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 10407642HCID 10407642, compound

Product 1

HCID 19880286HCID 19880286, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-6-benzoyloxy-8-methoxyquinoline (6.0 g) and 4-amino-m-cresol (2.0 g) were heated together under reflux in 1,4-dioxan (100 ml) for 2 hours. The solvent was evaporated and the residue heated on a steam bath in 10% methanolic potassium hydroxide for ten minutes. The solution was neutralized with 5M HCl and extracted several times with dichloromethane. The combined extracts were dried and evaporated to give 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-6-hydroxy-8-methoxyquinoline (4.0 g, 70%) m.p. 251°-253°.

Workup

  1. customThe solvent was evaporated
  2. temperaturethe residue heated on a steam bath in 10% methanolic potassium hydroxide for ten minutes
  3. extractionextracted several times with dichloromethane
  4. customThe combined extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-44ede19ccf334ec0b270e030cb15249e
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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