2,4-Dinitrobenzoic acid → 2,4-Dinitrobenzamide

Reaktionsgleichung

[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[NH4+:22].[OH-]>>[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:22])=[O:7])([O-:3])=[O:2]

Komponenten

Edukt 3

HCID 118802,4-Dinitrobenzoic acid

HCID 14923Ammonium Hydroxide

HCID 65578Oxalyl chloride

Produkt 1

HCID 37335182,4-DinitrobenzamideAusbeute 89 %

Versuchsvorschrift

2,4-Dinitrobenzoic acid (8.17 g, 38.5 mmol) was treated with oxalyl chloride (3.90 mL, 44.7 mmol). The resulting acid chloride was treated with saturated NH4OH solution (200 mL) to yield the title compound (7.25 g, 89%). m.p. 202°-204° C. 1H NMR (300 MHz, DMSO) δ8.75 (d, 1H), 8.58 (dd, 1H), 8.48 (br s, 1H), 7.99 (br s, 1H), 7.91 (d, 1H), 5.50-6.20 (br s, 2H). MS (DCI/NH3) m/e 229 (M+NH4)+.

Quellen und Nachweise

ORD-Eintrag: ord-31a6f5a7f71c4d809ae281e01e1ca844
Quelldatensatz: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05597823

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