Glycine → 2-(2,6-Dinitrobenzamido)acetic acid

Reaktionsgleichung

[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[N+](C1C=CC=C([N+]([O-])=O)C=1C(O)=O)([O-])=O.[NH2:31][CH2:32][C:33]([OH:35])=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:7])([O-:3])=[O:2]

Komponenten

Edukt 4

HCID 750Glycine

HCID 10340Sodium Carbonate

HCID 119206Benzoic acid, 2,6-dinitro-

HCID 222422992,6-Dinitrobenzoyl chloride

Produkt 1

HCID 867131032-(2,6-Dinitrobenzamido)acetic acid

Versuchsvorschrift

As shown in scheme G, 2,6-dinitrobenzoyl chloride prepared from 2,6-dinitrobenzoic acid is treated with glycine in the presence of sodium carbonate to yield 2-(2,6-dinitrobenzamido)acetic acid (intermediate 10). Treatment of intermediate 10 either with K18F or K19F gave 2-(2-fluoro-6-nitrobenzamido)acetic acid, which on reduction with indium powder in the presence of either acetic acid or acetic anhydride-acetic acid gave the corresponding 2-(2-amino-6-fluorobenzamido)acetic acid (compound 8) or 2-(2-acetamido-6-fluorobenzamido)acetic acid (compound 9) respectively.