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

HRID 1271190Notes

Reaction equation

HRID 1271190 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, 3 H), 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-71155090bd314dd1b755750b838dad47
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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