Quinoline → HCID 15692171, compound

HRID 1791830Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-:17])=[O:16])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](C(O)=O)=[CH:6]2.N1C2C(=CC=CC=2)C=CC=1>[Cr]([O-])([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-:17])=[O:16])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2

Participants

Conditions

Temperature: 225 °C

Procedure

The crude 5-methoxy-4-nitroindole-2-carboxylic acid (720 mg, 3.05 mmol), quinoline (9 ml) and copper chromite (180 mg) were stirred together. Nitrogen was gently bubbled through the mixture for 5 minutes, then the mixture was heated quickly to 225° C., and stirred at this temperature for 40 minutes under an atmosphere of nitrogen. The mixture was cooled to ambient temperature diluted with ethyl acetate (80 ml) and the insoluble material filtered off. The filtrate was extracted twice with aqueous hydrochloric acid (2M) and then with saturated aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was dried (MgSO4), evaporated and the residue purified by silica column chromatography eluting with dichloromethane to give 5-methoxy-4-nitroindole (129 mg, 22%).

Workup

customNitrogen was gently bubbled through the mixture for 5 minutes
temperatureThe mixture was cooled to ambient temperature
additiondiluted with ethyl acetate (80 ml)
filtrationthe insoluble material filtered off
extractionThe filtrate was extracted twice with aqueous hydrochloric acid (2M)
dry with materialThe ethyl acetate layer was dried (MgSO4)
customevaporated
customthe residue purified by silica column chromatography
washeluting with dichloromethane

Sources & evidence

ORD record: ord-f52778852eac4e26b387c74570a3fc2c
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074800B1

Reaction notes

Loading…