Methyl iodide → 5-amino-1,5-dimethyl-7,8-dihydro-6H-quinolin-2-one

HRID 1586983Notes

Reaction equation

HRID 1586983 reaction equation
[H-].[Na+].Cl.[NH2:4][C:5]1([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]2[NH:10][C:9](=[O:15])[CH:8]=[CH:7][C:6]1=2.CI.[C:19](O)(=O)/C=C/C(O)=O.[OH-].[Na+]>CN(C)C=O>[NH2:4][C:5]1([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]2[N:10]([CH3:19])[C:9](=[O:15])[CH:8]=[CH:7][C:6]1=2

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 444972Fumaric AcidHCID 18409094HCID 18409094, compound

Product 1

HCID 103977135-amino-1,5-dimethyl-7,8-dihydro-6H-quinolin-2-oneYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium hydride (50% in oil, 2.9 g), 5-amino-5,6,7,8-tetrahydro-5-methyl-2(1H)-quinolinone hydrochloride (5.43 g), and dimethylformamide (370 ml) was stirred at room temperature for 1.5 hrs. Methyl iodide (3.97 g) was added, and the mixture was allowed to stand at room temperature for 20 hrs. The reaction mixture was concentrated in vacuo, and the residue was washed with dichloromethane. The washings were concentrated, the residue was dissolved in a mixture of ethyl acetate and methanol and treated with 0.5 equivalents of fumaric acid. The precipitate (2.65 g) was combined with a 1.9 g-sample obtained in another experiment, and the combined material was treated with 5% sodium hydroxide solution and extracted with dichloromethane. The extract was concentrated. Recrystallization of the residue from ethyl acetate gave 2.1 g (23%) of product, mp 166°-167.5° C.

Workup

  1. waitto stand at room temperature for 20 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washthe residue was washed with dichloromethane
  4. concentrationThe washings were concentrated
  5. dissolutionthe residue was dissolved in a mixture of ethyl acetate and methanol
  6. customobtained in another experiment
  7. extractionextracted with dichloromethane
  8. concentrationThe extract was concentrated
  9. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-bee5b588a2014fdd98cbc238677c3253
Source dataset
uspto-grants-1993_06
Patent number
US05216164

Reaction notes

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