Methanol → Methyl 4-amino-3-nitrobenzoate

HRID 58182

Reaktionsgleichung

Reaktionsgleichung von HRID 58182
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].[CH3:18]O>>[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:18])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 74115Benzoic acid, 4-amino-3-nitro-

Produkt 1

HCID 3941008Methyl 4-amino-3-nitrobenzoateAusbeute 100 %

Versuchsvorschrift

Thionyl chloride (19.4 g, 164.85 mmol) was added to a solution of 4-amino-3-nitrobenzoic acid (20 g, 109.89 mmol) in methanol (200 mL) at 0° C. The resulting mixture was then refluxed for 12 h. The reaction mixture was allowed to cool to room temperature. The yellow solid precipitated was filtered and dried to afford the title compound (22 g, yield: 100%) as a solid. 1H-NMR (CDCl3, 300 MHz): δ 8.85 (d, 1H), 7.99 (dd, 1H), 6.83 (d, 1H), 6.40 (s, 2H), 3.90 (s, 3H).

Aufarbeitung

  1. temperatureThe resulting mixture was then refluxed for 12 h
  2. customThe yellow solid precipitated
  3. filtrationwas filtered
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-79ed0dcb95ec418b81cc09537c4377b9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

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