Methanol → 4-Hydroxy-3,3-dimethyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one

HRID 2071607Notes

Reaction equation

HRID 2071607 reaction equation
N[C:2]1[C:11]([CH3:13])([CH3:12])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C[OH:22]>[OH-].[Na+]>[OH:14][C:10]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2](=[O:22])[C:11]1([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 21395181HCID 21395181, compound

Product 1

HCID 214117374-Hydroxy-3,3-dimethyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-amino-3,4-dihydro-3,3-dimethyl-4-phenylquinolin-4-ol (5.32 g., 0.02 mole) in methanol (40 ml.) and 2N aqueous sodium hydroxide (20 ml. ) was heated under reflux for 6 hours. The mixture was poured onto water, extracted with chloroform and the combined extracts washed and dried (MgSO4). After removal of the solvent the residue was crystallised from toluene to give the title compound (4.73g., m.p. 185° - 187° C). [Found: C, 76.25, H, 6.6, N, 5.3% C17H17NO2 requires, 76.4, H, 6.4, N, 5.25%].

Workup

  1. temperatureunder reflux for 6 hours
  2. additionThe mixture was poured onto water
  3. extractionextracted with chloroform
  4. washthe combined extracts washed
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent the residue
  7. customwas crystallised from toluene

Sources & evidence

ORD record
ord-ee9b58a1690a488a981cf2f155740d1f
Source dataset
uspto-grants-1977_09
Patent number
US04048177

Reaction notes

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