Hydrochloric Acid → 2-Carbamoyl-3-nitrobenzoic acid

HRID 1409611

Reaktionsgleichung

Reaktionsgleichung von HRID 1409611
[OH-:1].[K+].[N+:3]([C:6]1[CH:16]=[CH:15][CH:14]=[C:8]2[C:9]([NH:11][C:12](=[O:13])[C:7]=12)=[O:10])([O-:5])=[O:4].Cl>O>[N+:3]([C:6]1[CH:16]=[CH:15][CH:14]=[C:8]([C:9]([OH:1])=[O:10])[C:7]=1[C:12]([NH2:11])=[O:13])([O-:5])=[O:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 117793-NitrophthalimideHCID 14797Potassium Hydroxide

Produkt 1

HCID 4375472-Carbamoyl-3-nitrobenzoic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0° C. The suspension was stirred at 0° C. for 3 hours, and then heated to 30° C. for 3 hours. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0° C. for 1 hour. The suspension was filtered and washed with cold water (2×10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) δ 7.69 (brs, 1H, NHH), 7.74 (t, J=8 Hz, 1H, Ar), 7.92 (dd, J=1, 8 Hz, 1H, Ar), 8.13 (dd, J=1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) δ 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

Aufarbeitung

  1. temperatureheated to 30° C. for 3 hours
  2. temperatureThe resulting suspension was cooled to 0° C. for 1 hour
  3. filtrationThe suspension was filtered
  4. washwashed with cold water (2×10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-a16910e9ae8c466ab4aaff5072273bd9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921385B2

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