4-Amino-m-cresol → HCID 10020530, compound

HRID 1534490Notes

Reaction equation

HRID 1534490 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[CH:17]=[CH2:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:19][C:20]1[C:21]([CH3:27])=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1>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[CH:17]=[CH2:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 10015445HCID 10015445, compound

Product 1

HCID 10020530HCID 10020530, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-vinylquinoline (20.0 g, 77 mmol) and 4-amino-m-cresol (9.5 g, 77 mmol) were heated together under reflux in 1,4-dioxan (150 ml) for 2.5 hours. The solvent was evaporated and the residue was dissolved in dichloromethane, washed with water, 2M hydrochloric acid, sodium hydrogen carbonate solution and brine. The solution was dried (anhyd. MgSO4), filtered and evaporated to an oil which was chromatographed (silica gel, 1% methanol in dichloromethane) to give 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-8-vinylquinoline as orange crystals (9.0 g, 32%) m.p. 150°-2°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water, 2M hydrochloric acid, sodium hydrogen carbonate solution and brine
  4. dry with materialThe solution was dried (anhyd. MgSO4)
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customwas chromatographed (silica gel, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-22155be3a70742b7bdbb13634e6a4b31
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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