2-Bromopropane → 7-Chloro-5-iodo-8-[(propan-2-yl)oxy]quinoline

HRID 872238Notes

Reaction equation

HRID 872238 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([I:13])[CH:3]=1.Br[CH:15]([CH3:17])[CH3:16]>>[Cl:1][C:2]1[C:11]([O:12][CH:15]([CH3:17])[CH3:16])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([I:13])[CH:3]=1

Participants

3

Reactant 2

HCID 63582-BromopropaneHCID 1419447-Chloro-5-iodo-8-quinolinol

Product 1

HCID 597569557-Chloro-5-iodo-8-[(propan-2-yl)oxy]quinolineYield 80%

Procedure

Following the procedure described in Example 8, 7-chloro-5-iodo-8-hydroxy-quinoline 20 and 2-bromopropane gave 7-chloro-5-iodo-8-isopropoxy-quinoline 21 (80%). 1H NMR (CDCl3/DMSO-d6 (19:1), 400 MHz): δ 9.09 (m, 1 H), 8.55 (m, 1 H), 8.10 (s, 1 H), 7.63 (m, 1 H), 5.15 (m, 1 H), 1.49 (s, 3 H), 1.47 (s, 3 H).

Sources & evidence

ORD record
ord-1f67070450cb42988d30276df3c3854e
Source dataset
uspto-grants-2015_03
Patent number
US08975278B2

Reaction notes

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