3,4-Dimethoxy-6-nitrobenzamide → 2-Amino-4,5-dimethoxybenzamide

HRID 276793

Reaktionsgleichung

Reaktionsgleichung von HRID 276793
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[C:7]([N+:16]([O-])=O)[CH:6]=1>CO.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:3][O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[C:7]([NH2:16])[CH:6]=1

Komponenten

5

Edukt 2

HCID 27361933,4-Dimethoxy-6-nitrobenzamideHCID 4311764Sodium borohydride

Produkt 1

HCID 108672362-Amino-4,5-dimethoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

NaBH4 (400 mg) was added with stirring over 4 hours to a solution of 4,5-dimethoxy-2-nitrobenzamide 2 (1.58 g; 7 mmol) in MeOH containing catalytic amount of CuSO4. The reaction mixture was poured into ice-water (200 mL) with stirring to give 4,5-dimethoxy-2-aminobenzamide 3 which was directly refluxed with HCOOH (20 mL) for 5 hours. After removal of solvent, the residue was recrystallized from DMF to give pure crystals 4 (1.18 g; 81.5%). m.p. 295.0-297.0° C.; 1H NMR (DMSO-d6): δ 12.03 (br, s, 1H, —NH), 7.99 (s, 1H, 2-H), 7.42 (s, 1H, 5-H), 7.11 (s, 1H, 8-H), 3.88, 3.85 (s, s, 6H, —OCH3); IR(KBr)υmax: 3015, 2840, 1648, 1504, 1261, 1070 cm−1; GC/MS m/z 206(M+, 100), 191(M+ —CH3, 31.5), 163(16.7), 120(15.2).

Quellen und Nachweise

ORD-Eintrag
ord-898ad032d9fd45d48d8d7223f8a87e6f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355645B2

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