Quinoline, 1,2,3,4-tetrahydro-6-methoxy- → 8-Bromo-6-methoxy-1,2,3,4-tetrahydroquinoline

HRID 2251055Notes

Reaction equation

HRID 2251055 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2.[Br-:13].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[NH:9][CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-HCID 21124087Pyridiniumtribromide

Product 1

HCID 184528218-Bromo-6-methoxy-1,2,3,4-tetrahydroquinolineYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A: A solution of 6-methoxy-1,2,3,4-tetrahydroquinoline (6.19 g, 37.9 mmol) in CH2Cl2 (76 mL) was treated with pyridinium tribromide (25.42 g, 79.7 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL). The dichloromethane was separated, dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent to give 8-bromo-6-methoxy-1,2,3,4-tetrahydroquinoline (2.93 g, 32% yield): 1H NMR (300 MHz, CDCl3): δ 6.88 (s 1 H), 6.55 (s, 1 H), 3.71 (s, 3H), 3.37-3.33 (t, J=6.6, 2 H), 2.78-2.74 (t, 2 H), 1.97-1.89 (m, 2 H); LRMS (AP+) for (M+H)+: for C10H12NOBr Calculated: 241.1 found: 241.0.

Workup

  1. customThe reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL)
  2. customThe dichloromethane was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-5ca96cc8fdfb4b18b6c6fe1758d577d3
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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