N-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetamide → 7-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 2247225Notes

Reaction equation

HRID 2247225 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8]([NH:12]C(=O)C)=[CH:9][CH:10]=2)[NH:5][C:4](=[O:16])[CH2:3]1>Cl.CCO>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH3:17])([CH3:1])[CH2:3][C:4](=[O:16])[NH:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 14476477N-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetamide

Product 1

HCID 144764787-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

N-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-acetamide (1.50 g, 6.46 mmol) in 10 ml of HCl (concentrated, 37%) and 30 ml of EtOH was stirred at 75° C. for 4 h. The solvents were removed under reduced pressure. The residue was dissolved in EtOAc/H2O, neutralized with NaHCO3, washed with brine, dried with Na2SO4, filtered, and condensed to give the titled compound as an off-white solid.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc/H2O
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customcondensed

Sources & evidence

ORD record
ord-b600533ae3f54bf8aea941dd71dde39b
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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