Potassium Iodide → 3-(Quinolin-4-yloxy)propan-1-ol

HRID 40797

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:21][CH2:22][CH2:23][OH:24]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][CH2:21][CH2:22][CH2:23][OH:24])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of quinolin-4-ol (1.35 g, 9.30 mmol), anhydrous potassium carbonate (3.73 g, 26 mmol) and potassium iodide (4.23 g) in anhydrous DMF (8 mL) was stirred at 25° C. for 30 minutes. 3-Chloropropanol (2.93 g, 31 mmol) was added and the reaction was stirred until the starting material was consumed. The reaction was diluted with dichloromethane and extracted with water. The product was obtained as a slightly yellow solid (0.5298 g, 28%) after evaporation of the dichloromethane layer, and was used for the next step without further purification. 1H NMR (400 MHz, CDCl3): 2.09 (2H, m), 3.93 (2H, t, J=5.6 Hz), 4.10 (2H, t, J=5.6 Hz), 4.51 (11H, s), 6.25 (1H, d, J=5.5 Hz), 7.32 (1H, t, J=7.4 Hz), 7.56 (1H, t, J=8.2 Hz), 7.90 (1H, d, J=8.4 Hz), 7.93 (1H, d, J=8.4 Hz), 8.36 (1H, d, J=5.3 Hz).

Workup

stirringthe reaction was stirred until the starting material
customwas consumed
additionThe reaction was diluted with dichloromethane
extractionextracted with water

Sources & evidence

ORD record: ord-d91781c33a6f4b49b78e7d1ae719acf2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530491B2

Linked notes

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