8-Chloro-2-(pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylic acid ethyl ester → 8-Chloro-2-(pyridin-3-yl)quinoline-3-carboxylic acid ethyl ester

HRID 572121Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:16])[CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=[O:5])[CH3:2]>ClC1C=CC=CC=1.O=[Mn]=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 8-chloro-2-(pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (10.7 g, 34 mmol) in chlorobenzene (60 mL) was treated with MnO2 (10 g) and the mixture was heated to 60° C. for 3 h. The mixture was filtered through a celite plug and concentrated in vacuo. The residue was washed with diethyl ether to give 8-chloro-2-(pyridin-3-yl)quinoline-3-carboxylic acid ethyl ester (8.4 g, 79%) as a white solid. δH (CDCl3) 8.96 (d, J 1.7 Hz, 1H), 8.83 (s, 1H), 8.75 (dd, J 5.0, 1.1 Hz, 1H), 8.27 (dt, J 7.9, 1.7 Hz, 1H), 8.00 (dd, J 7.5, 1.0 Hz, 1H), 7.92 (dd, J 8.2, 1.0 Hz, 1H), 7.60 (m, 2H), 4.32 (q, J 7.1 Hz, 2H), 1.24 (t, J 7.1 Hz, 3H). LCMS (ES+) 313.2 (M+H)+.

Workup

filtrationThe mixture was filtered through a celite plug
concentrationconcentrated in vacuo
washThe residue was washed with diethyl ether

Sources & evidence

ORD record: ord-85b3eec63cb74ad89973f1cd954ccfa6
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029392B2

Reaction notes

Loading…