Imidazole → 2-Chloro-3-(iodomethyl)-8-methylquinoline

HRID 1948730Notes

Reaction equation

HRID 1948730 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12]O)=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:34]I.N1C=CN=C1>C(Cl)Cl>[Cl:1][C:2]1[C:11]([CH2:12][I:34])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 865104(2-Chloro-8-methylquinolin-3-yl)methanol

Product 1

HCID 873073252-Chloro-3-(iodomethyl)-8-methylquinolineYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-chloro-8-methylquinolin-3-yl)methanol (2.0 g, 10 mmol) in DCM (200 mL) were added triphenylphosphine (2.6 g, 10 mmol), iodine (2.6 g, 10 mmol) and imidazole (0.7 g, 10 mmol) and the reaction mixture was stirred for 2 h at r.t. The mixture was washed with water (50 mL) and the organic layer was separated, dried and concentrated in vacuo. Purification by column chromatography (SiO2, 50% Et2O in heptane) gave the title compound as a brown solid (2.2 g, 72%). δH (CDCl3) 8.17 (s, 1H), 7.62 (d, J 9 Hz, 1H), 7.55 (d, J 9 Hz, 1H), 7.45 (t, J 9 Hz, 1H), 4.68 (s, 2H), 2.75 (s, 3H). LCMS (ES+) 318.0, 320.0 (M+H)+, RT 4.53 minutes (Method 3).

Workup

  1. washThe mixture was washed with water (50 mL)
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 50% Et2O in heptane)

Sources & evidence

ORD record
ord-96f0eca424fe491285d6ced19efc7790
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

Loading…