Dimethylamine → HCID 59441838, compound

HRID 1014381Notes

Reaction equation

HRID 1014381 reaction equation
Br[CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[C:8]([CH3:21])([CH3:20])[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:28][NH:29][CH3:30]>O1CCCC1.O>[CH3:20][C:8]1([CH3:21])[C:9]2[C:14](=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([O:18][CH3:19])[CH:10]=2)[N:5]([C:3](=[O:4])[CH2:2][N:29]([CH3:30])[CH3:28])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 59441858HCID 59441858, compound

Product 1

HCID 59441838HCID 59441838, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(bromoacetyl)-4,4-dimethyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (1.0 g, 2.8 mmol) in tetrahydrofuran (35 mL) was treated with potassium carbonate (1.3 g, 9.4 mmol) and dimethyl amine (10 mL, 20 mmol, 2 M in THF, Aldrich). The mixture was heated in sealed tube at 55° C. for 1h, cooled, diluted with water, and extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated to give {2-[4,4-dimethyl-6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine which was taken directly to the next step. ESIMS (M+H)+=322.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a22d2c0df11c4777b87bb9ac1497df6c
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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