Iodoethane → 6-Chloro-4-ethoxy-3-iodo-7-methoxy-2-methylquinoline

HRID 1908992Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([CH3:14])=[C:6]([I:15])[C:5]2=[O:16].C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[C:6]([I:15])=[C:5]2[O:16][CH2:23][CH3:24]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 6-chloro-3-iodo-7-methoxy-2-methylquinolin-4(1H)-one (2.00 g, 5.72 mmol) in dimethylformamide (57 ml) was added potassium carbonate (1.58 g, 11.4 mmol) at room temperature. The resulting suspension was stirred 0.5 hours at 50° C. Ethyl iodide was added dropwise at room temperature, and the reaction mixture was stirred 8 hours at 50° C. The solvent was removed in vacuo and the resulting residue was resuspended in ethyl acetate and water. The organic layer was extracted with brine, dried over magnesium sulfate and concentrated in vacuo to give 2.12 g (99% yield) of 6-chloro-4-ethoxy-3-iodo-7-methoxy-2-methylquinoline as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 7.99 (s, 1H), 7.40 (s, 1H), 4.19 (q, J=7.1 Hz, 2H), 4.02 (s, 3H), 2.92 (s, 3H), 1.61 (t, J=7.1 Hz, 3H).

Workup

stirringthe reaction mixture was stirred 8 hours at 50° C
customThe solvent was removed in vacuo
extractionThe organic layer was extracted with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8fe9fa27a84147b9b0bd14ed9b369ff3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598354B2

Reaction notes

Loading…