Potassium Iodide → 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone

HRID 1922458Notes

Reaction equation

HRID 1922458 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13]Cl)[CH2:7][CH2:6][CH2:5]2.[I-].[K+].[CH3:18][NH:19][CH2:20][CH3:21]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][N:19]([CH2:20][CH3:21])[CH3:18])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 12219N-MethylethylamineHCID 573433941-(6-Bromo-3,4-dihydro-1(2H)-quinolinyl)-2-chloroethanone

Product 1

HCID 573435551-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanoneYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-chloroethanone (1 g, 3.47 mmol) and potassium iodide (0.115 g, 0.693 mmol) in 10 mL THF was treated with N-methylethanamine (1.786 mL, 20.79 mmol). The mixture was stirred at room temperature for 2 hours then heated at 65° C. for 1 hour. The mixture was concentrated and partitioned between CH2Cl2 (100 mL) and saturated sodium bicarbonate (25 mL). After extraction, the organic layer was separated, dried over Na2SO4, filtered and concentrated to give a light brown residue. This residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in methanol/95% CH2Cl2 to give a light brown residue (1.06 g, 98%). 1H-NMR (CDCl3) δ 7.52-7.40 (br s, 1H), 7.30-7.27 (m, 2H), 3.80 (t, J=6.0 Hz, 2H), 3.28 (s, 2H), 2.72 (t, J=6.9 Hz, 2H), 2.50 (quart, J=7.2 Hz, 2H), 2.30 (s, 3H), 1.96 (quint, J=6.6 Hz, 2H), 1.03 (t, J=7.2 Hz, 3H). MS (ESI): 311.1 and 313.1 (M+1, 100%).

Workup

  1. temperaturethen heated at 65° C. for 1 hour
  2. concentrationThe mixture was concentrated
  3. custompartitioned between CH2Cl2 (100 mL) and saturated sodium bicarbonate (25 mL)
  4. extractionAfter extraction
  5. customthe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a light brown residue

Sources & evidence

ORD record
ord-2f9d8bcc0b83436fa7ce65605cceeb03
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…