Hydrochloric Acid → 4-(6-Bromo-3,4-dihydroquinolin-1(2H)-yl)cyclohexanone

HRID 1922522Notes

Reaction equation

HRID 1922522 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:21][CH2:20][C:15]3(OCC[O:16]3)[CH2:14][CH2:13]1)[CH2:7][CH2:6][CH2:5]2.Cl>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]1)[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59807078HCID 59807078, compound

Product 1

HCID 598070354-(6-Bromo-3,4-dihydroquinolin-1(2H)-yl)cyclohexanoneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 4 (0.21 g, 0.596 mmol) in acetone (5 mL) was treated with 10% HCl solution (5 mL) and the resulting mixture was stirred for overnight (16 h). Acetone was evaporated, the crude was basified with 2 N NaOH solution and the product was extracted into CH2Cl2 (2×15 mL). The combined CH2Cl2 layer was washed with brine (10 mL) and dried (Na2SO4). The solvent was evaporated to obtain compound 5 (0.18 g, 98%) as a syrup. 1H NMR (CDCl3) δ 7.16 (dd, 1H, J=2.4, 4.3 Hz), 7.08 (s, 1H), 6.60 (d, 1H, J=9.0 Hz), 4.11-4.01 (m, 1H), 3.17 (t, 2H, J=5.7 Hz), 2.71 (t, 2H, J=6.3 Hz), 2.52-2.48 (m, 4H), 2.14-1.85 (m, 6H); ESI-MS (m/z, %): 308, 310 (MH+, 100).

Workup

  1. customAcetone was evaporated
  2. extractionthe product was extracted into CH2Cl2 (2×15 mL)
  3. washThe combined CH2Cl2 layer was washed with brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a73dca011a7e45c6bf8be19e84a97223
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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