Hydrogen Peroxide → Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate

HRID 906181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906181
[NH2:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].OO.C(=O)([O-])[O-:18].[K+].[K+]>CS(C)=O>[NH2:1][C:2]1[C:3]([C:13]([NH2:14])=[O:18])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67402842Methyl 5-amino-4-cyano-2-methylbenzoate

Produkt 1

HCID 67403771Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoateAusbeute 208 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Methyl 5-amino-4-cyano-2-methylbenzoate (151 mg, 0.79 mmol) (synthesized according to reagent preparation 41) was dissolved in DMSO (1.5 mL). 30% Aqueous hydrogen peroxide (0.3 mL) and potassium carbonate (35 mg, 0.25 mmol) were added, and the mixture was stirred at ambient temperature for 1.5 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted (2×) with ethyl acetate. The combined organic portion was dried over sodium sulfate, filtered and concentrated to a yellow oil which was purified by preparative reverse phase HPLC to afford methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate (108 mg, 0.52 mmol, 66% yield). NMR (400 MHz, CDCl3): δ 7.85 (s, 1H), 7.45 (br s, 1H), 7.26 (s, 1H), 7.19 (br s, 1H), 6.48 (s, 2H), 3.80 (s, 3H), 2.32 (s, 3H); MS (EI) for C10H12N2O3: 209 (MH+).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous portion was extracted (2×) with ethyl acetate
  3. dry with materialThe combined organic portion was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil which
  6. customwas purified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-681ce2a519fd405591d2cd681d47038d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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