Borane;tetrahydrofuran → 6-Bromo-1-(2-chloroethyl)-1,2,3,4-tetrahydroquinoline

HRID 1922487Notes

Reaction equation

HRID 1922487 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=O)[CH2:13][Cl:14])[CH2:7][CH2:6][CH2:5]2.B.C1COCC1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][Cl:14])[CH2:7][CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 573433941-(6-Bromo-3,4-dihydro-1(2H)-quinolinyl)-2-chloroethanone2×

Product 1

HCID 573433956-Bromo-1-(2-chloroethyl)-1,2,3,4-tetrahydroquinolineYield 100%

Procedure

A round bottom flask was charged with 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-chloroethanone (compound 1, 0.546 g, 1.892 mmol) and treated with borane-THF complex (1M in THF, 18.9 mL, 18.9 mmol, 10 equivalents) and the resulting mixture stirred overnight at room temperature. After cooling to 0° C., the reaction was quenched by dropwise addition of methanol (5 mL) and stirred for 10 minutes at 0° C. The mixture was concentrated under reduced pressure and purified directly on silica gel eluting with 10% ethyl acetate/90% hexanes to yield a viscous residue, 2 (0.519 g, 100%). 1H-NMR (CDCl3) δ 7.11 (dd, 1H, J=8.7, 2.4 Hz), 7.08-7.04 (m, 1H), 6.42 (d, 1H, J=8.7), 3.64-3.56 (m, 4H), 3.35 (t, 2H, J=5.6 Hz), 2.73 (t, 2H, J=6.3 Hz), 1.97-1.89 (m, 2H). MS (ESI+): 274/276 (MH+, 100).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction was quenched by dropwise addition of methanol (5 mL)
  3. stirringstirred for 10 minutes at 0° C
  4. concentrationThe mixture was concentrated under reduced pressure
  5. custompurified directly on silica gel eluting with 10% ethyl acetate/90% hexanes

Sources & evidence

ORD record
ord-ab590697f9184a3c82b57aa0f84c8db8
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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