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

HRID 1647475Notes

Reaction equation

HRID 1647475 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-544dc2e42f7049d0ab9a0f51b2d1404b
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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