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Dimethylformamide → 6-Methyl-2-nitrobenzoic acid

HRID 69309
Notes
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Reaction equation

HRID 69309 reaction equation
[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]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoate

Product 3

HCID 160976-Methyl-2-nitrobenzoic acidHCID 67184N-bromobutanimide
HCID 15088701
Methyl 2-(bromomethyl)-4-nitrobenzoate

Procedure

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.

Sources & evidence

ORD record
ord-2aa42e2d16a7451995b8d9779e985718
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822499B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes