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

HRID 1802124Notes

Reaction equation

HRID 1802124 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 mg1.57 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-ee4b03fde69748198038efa7e82c1223
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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