1-Iodoheptane → 6-Bromo-2-(heptyloxy)quinoline

HRID 709908Notes

Reaction equation

HRID 709908 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.I[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 202741-IodoheptaneHCID 178515482HCID 178515482, compound

Product 1

HCID 674087426-Bromo-2-(heptyloxy)quinoline

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 6-bromoquinolin-2-ol (352 mg 1.57 mmol) and silver carbonate (863 mg, 3.14 mmol, 2.0 eq.) in toluene (20 mL) was added 1-iodoheptane (355 mg, 1.57 mmol, 1.0 eq.) and stirred for 3 h at 110° C. The reaction mixture was evaporated under reduced pressure to remove most of solvent, then filtered, and washed with ethyl acetate. The filtrate was concentrated to give crude the title compound. The crude product was purified by flash chromatography using PE/EA (20/1) as eluent to give product as a red oil (300 mg, 60%). ESI-MS: 323.8 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ: 7.84-7.83 (m, 2H), 7.70-7.68 (m, 2H), 6.89 (d, 1H), 4.43 (t, 2H), 1.81 (q, 2H), 1.51-1.28 (m, 8H), 0.90 (t, 3H).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto remove most of solvent
  3. filtrationfiltered
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7e9ff2dd6f924e4e8f22ed478cfa2071
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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