5-Chloro-2-nitrobenzoic acid → 3-Amino-5-chloro-2-nitrobenzoic acid

HRID 44500

Reaktionsgleichung

Reaktionsgleichung von HRID 44500
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14].CO[NH2:22].Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:22][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=[C:8]([Cl:7])[CH:9]=1)[C:13]([OH:15])=[O:14]

Komponenten

6

Edukt 3

HCID 172865-Chloro-2-nitrobenzoic acidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 107274793-Amino-5-chloro-2-nitrobenzoic acidAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under nitrogen, to a solution of t-BuOK (156.8 g) and Cu(OAc)2 (3.6 g) in DMF (1.2 L) was added a solution of 5-chloro-2-nitrobenzoic acid (40.0 g) and MeONH2HCl (33.2 g) in DMF (300 mL) at 0° C. After 3 h the reaction was quenched by addition of H2O (2.5 L) and acidified with 10% HCl solution to pH=1. The mixture was extracted with EA (2 L×2) and the combined organic layers were then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in-vacuo to afford the crude product as a yellow solid (43.2 g, yield 100%). 1H NMR (300 MHz, CDCl3): δ ppm 6.88 (s, 1H, J=2.4 Hz), 6.91 (d, 1H, J=2.4 Hz), 8.08 (br s, 2H); LC-MS: m/e=217 [M+1]+.

Aufarbeitung

  1. customAfter 3 h the reaction was quenched by addition of H2O (2.5 L)
  2. extractionThe mixture was extracted with EA (2 L×2)
  3. washthe combined organic layers were then washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2e39807bb5a247ceb9d93ca56ec7de94
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541411B2

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