4-Amino-m-cresol → HCID 10042634, compound

HRID 1885188Notes

Reaction equation

HRID 1885188 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([OH:17])=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:18][C:19]1[C:20]([CH3:26])=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=1[CH3:26])=[CH:13][C:12]([OH:17])=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 10377395HCID 10377395, compound

Product 1

HCID 10042634HCID 10042634, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-6-hydroxyquinoline (4.0 g) and 4-amino-m-cresol (2.0 g) were heated together under reflux in 1,4-dioxan (60 ml) for 2 hours. The solvent was evaporated and the residue was dissolved in chloroform and washed successively with 2M HCl, sodium hydrogen carbonate solution (×2) and brine. The organic solution was dried, filtered and evaporated to a brown oil. A quantity of solid material that appeared insoluble in chloroform was combined with the oil and the mixture was chromatographed (silica gel, 2-4% methanol in chloroform) to give 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-6-hydroxyquinoline (1.3 g, 24%) as orange crystals, m.p. 242°-244°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed successively with 2M HCl, sodium hydrogen carbonate solution (×2) and brine
  4. customThe organic solution was dried
  5. filtrationfiltered
  6. customevaporated to a brown oil
  7. customthe mixture was chromatographed (silica gel, 2-4% methanol in chloroform)

Sources & evidence

ORD record
ord-fa502cfbaa394ec2b99be966071c5a17
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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