Dimethylformamide → 6-Methyl-2-nitrobenzoic acid

HRID 69309

Reaktionsgleichung

Reaktionsgleichung von HRID 69309
[CH2:1]1[CH:8](N)[C:6](=[O:7])[NH:5][C:3](=[O:4])C1.Cl.[Br:11][CH2:12][C:13]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C.CN(C)C=[O:36]>>[Br:11][CH2:12][C:13]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].[N+:23]([C:21]1[CH:20]=[CH:19][CH:14]=[C:13]([CH3:12])[C:22]=1[C:6]([OH:7])=[O:36])([O-:25])=[O:24].[Br:11][N:5]1[C:6](=[O:7])[CH2:8][CH2:1][C:3]1=[O:4]

Komponenten

7

Versuchsvorschrift

This compound can be prepared according to the methods described in U.S. Pat. Nos. 6,281,230 and 5,635,517, the entireties of which are incorporated herein by reference. For example, the compound can be prepared through catalytic hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 3-(4-Nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione can be obtained by allowing 2,6-dioxopiperidin-3-ammonium chloride to react with methyl 2-bromomethyl-4-nitrobenzoate in dimethylformamide in the presence of triethylamine. The methyl 2-bromomethyl-4-nitrobenzoate in turn is obtained from the corresponding methyl ester of nitro-ortho-toluic acid by conventional bromination with N-bromosuccinimide under the influence of light.

Quellen und Nachweise

ORD-Eintrag
ord-2aa42e2d16a7451995b8d9779e985718
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822499B2

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