2-Amino-4-chlorobenzaldehyde → 7-Chloro-2-(2-methoxycarbonylbenzofuran-5-yl)quinoline

HRID 2258522Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]=2[CH:16]=1)(=O)[CH3:2].[NH2:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH:20]=O>C(Cl)(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:26][C:24]1[CH:25]=[C:18]2[C:19]([CH:20]=[CH:2][C:1]([C:4]3[CH:5]=[CH:6][C:7]4[O:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]=4[CH:16]=3)=[N:17]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 5-acetyl-2-methoxycarbonylbenzofuran (0.57 g), 2-amino-4-chlorobenzaldehyde (0.40 g) and p-toluenesulfonic acid monohydrate (0.04 mg) was stirred at 200° C. for 3 hours. After being cooled, the resulting mixture was dissolved in chloroform, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and toluene (1:20). The fractions containing object compound were combined and concentrated under reduced pressure to give 7-chloro-2-(2-methoxycarbonylbenzofuran-5-yl)quinoline (0.32 g).

Workup

temperatureAfter being cooled
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a syrup
washeluted with a mixture of ethyl acetate and toluene (1:20)
additionThe fractions containing object compound
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8acab26d07264a049ec02b6d65c7d79a
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05661159

Reaction notes

Loading…