Chloroacetyl chloride → 1-(6-Bromo-3,4-dihydro-1(2H)-quinolinyl)-2-chloroethanone

HRID 1922457Notes

Reaction equation

HRID 1922457 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[Cl:12][CH2:13][C:14](Cl)=[O:15].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:14](=[O:15])[CH2:13][Cl:12])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 47150296-Bromo-1,2,3,4-tetrahydroquinoline

Product 1

HCID 573433941-(6-Bromo-3,4-dihydro-1(2H)-quinolinyl)-2-chloroethanone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-bromo-1,2,3,4-tetrahydroquinoline (2.09 g, 9.85 mmol) in 55 mL toluene was treated with 2-chloroacetyl chloride (0.863 mL, 10.84 mmol) dropwise over 10 minutes. The resulting suspension was stirred at room temperature for 1.5 hour then heated at 95° C. for 30 minutes. After cooling to room temperature, the yellow solution was diluted with 20 mL ethyl acetate and treated with 25 mL of a saturated aqueous sodium bicarbonate solution. The mixture was poured into a separatory funnel and extracted. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel using 30% ethyl acetate:70% hexanes as eluant. A white solid was obtained after drying under reduced pressure (Yield: 2.4 g, 84%). 1H-NMR (CDCl3) δ 7.35-7.33 (m, 3H), 4.19 (s, 2H), 3.80 (t, J=6.3 Hz, 2H), 2.74 (t, J=6.6 Hz, 2H), 2.04-1.98 (m, 2H).

Workup

  1. temperaturethen heated at 95° C. for 30 minutes
  2. temperatureAfter cooling to room temperature
  3. additionThe mixture was poured into a separatory funnel
  4. extractionextracted
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography on silica gel using 30% ethyl acetate
  10. customA white solid was obtained
  11. customafter drying under reduced pressure (Yield: 2.4 g, 84%)

Sources & evidence

ORD record
ord-0dd4ccb9fefc4a06b504f6a85a195ab2
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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