2-Methylquinoline → 2-[2-(3-Nitrophenyl)ethenyl]quinoline

HRID 1088453Notes

Reaction equation

[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH3:3].[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13]>C(OC(=O)C)(=O)C>[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH:3]=[CH:18][C:17]1[CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of quinaldine (8 g) and m-nitrobenzaldehyde (8.4 g) in acetic anhydride (24 ml) was stirred at 130° C. overnight. The mixture was cooled to room temperature and poured into aqueous pH 7 buffer (250 ml). The solid was chromatographed on column of flash silica gel using as eluant dichloromethane to afford a solid which was recrystallized from ethyl acetate to afford the title product as a yellow solid: m.p. 145-147° C.

Workup

temperatureThe mixture was cooled to room temperature
additionpoured into aqueous pH 7 buffer (250 ml)
customThe solid was chromatographed on column of flash silica gel using as eluant dichloromethane
customto afford a solid which
customwas recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-ea2c77fe15ed4feeabab1d9ef85e93f4
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04962203

Reaction notes

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