4-Nitroanthranilic acid → Methyl 4-nitroanthranilate

HRID 29659

Reaktionsgleichung

Reaktionsgleichung von HRID 29659
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-:3])=[O:2].[Si](C=[N+]=[N-])(C)(C)[CH3:15]>C1C=CC=CC=1.CO>[CH3:15][O:9][C:8](=[O:10])[C:7]1[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[NH2:13]

Komponenten

4

Edukt 2

HCID 120764-Nitroanthranilic acidHCID 167693Trimethylsilyldiazomethane

Produkt 1

HCID 596476Methyl 4-nitroanthranilateAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21927730Benzene methanolLösungsmittel

Versuchsvorschrift

To a solution of 4-nitro-anthranilic acid (2.200 g, 10.9 mmol, 1 eq) in benzene/methanol (4/1) (100 mL) was added TMSCHN2 (2M in hexanes) (12 mL, 24 mmol, 2.2 eq). The reaction was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 4-nitro-anthranilic acid methyl ester (1.841 g, 86%) as a bright yellow solid. 1H NMR (300 MHz, CDCl3); δ 8.00 (d, 1H), 7.50 (d, 1H), 7.40 (dd, 1H), 3.92 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c4c7adf42b564347b9dd32ea4aedb73c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420083B2

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