Dimethylamine → {2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine

HRID 1014298Notes

Reaction equation

HRID 1014298 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[NH:10][CH2:9][CH2:8][CH2:7]2)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25](Cl)=[O:26].[CH3:28][NH:29][CH3:30].C1COCC1>ClCCl.C(=O)(O)[O-].[Na+].O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[N:10]([C:25](=[O:26])[CH2:24][N:29]([CH3:30])[CH3:28])[CH2:9][CH2:8][CH2:7]2)[CH3:2]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 594418676-(Ethyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 59441935{2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamineYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of 6-(ethyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (5.0 g, 22.50 mmol) and potassium carbonate (6.22 g, 45.0 mmol) in dichloromethane (100 mL) was treated with bromoacetylchloride (2.336 mL, 28.1 mmol) and stirred for 25 minutes. Water was added and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, redissolved in THF, and 2.0M dimethyl amine in THF (67.5 mL, 135 mmol) was added. The solution was stirred overnight, diluted with saturated sodium bicarbonate, and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford {2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine (5.8 g, 84% yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.34 (s, 1 H), 7.16 (s, 1 H), 4.17 (q, J=6.96 Hz, 2 H), 3.74 (t, J=5.62 Hz, 2 H), 3.21 (s, 2 H), 2.80 (t, J=6.32 Hz, 2 H), 2.21 (s, 6 H), 1.76-2.01 (m, 2 H), 1.33 (t, J=6.92 Hz, 3 H).

Workup

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. dissolutionredissolved in THF
  4. stirringThe solution was stirred overnight
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-b8a06e30b62f4c399796fbacd44d8fcf
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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