Tetrahydrofuran → HCID 67404328, Verbindung

HRID 906098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906098
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13].O1CCC[CH2:16]1.C[Si](C=[N+]=[N-])(C)C>CO>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 167693TrimethylsilyldiazomethaneHCID 53406085HCID 53406085, Verbindung

Produkt 1

HCID 67404328HCID 67404328, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-Amino-2-methyl-3-nitrobenzoic acid (1.87 g, 9.54 mmol) was solubilized in methanol (100 mL) and tetrahydrofuran (100 mL) and was treated with (trimethylsilyl)diazomethane solution (5.3 mL, 10.5 mmol, 2.0M in diethyl ether). After the reaction was shown to be complete, the mixture was concentrated and the residue was purified via column chromatography (silica gel, 5:1 hexanes/ethyl acetate) to give 1.10 g (55% yield) of methyl 4-amino-2-methyl-3-nitrobenzoate. 1H NMR (400 MHz, d6-DMSO): 7.73 (d, 1H), 6.75 (d, 1H), 6.51 (broad s, 2H), 3.75 (s, 3H), 2.37 (s, 3H). MS (EI) for C9H10N2O4: 210 (MH+).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified via column chromatography (silica gel, 5:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d352edf749c441fab6153364f6edaa18
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

Notizen zur Reaktion

Wird geladen…