Nitric Acid → N-(2-ethyl-6-nitrophenyl)acetamide

HRID 471613

Reaktionsgleichung

Reaktionsgleichung von HRID 471613
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:6].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C.O>[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:1]([O-:4])=[O:2])[C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:6]

Komponenten

7

Edukt 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 36332O-Ethylacetanilide

Produkt 1

HCID 14147006N-(2-ethyl-6-nitrophenyl)acetamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of nitric acid (4.2 mL) in glacial acetic acid (5.2 mL)) was added drop wise to solution of N-(2-ethylphenyl)acetamide (Example 139f)(1.00 g, 6.13 mmol) in AcOH (22 mL) and acetic anhydride (18 mL) at 0° C. The reaction was stirred at 0° C. for 1 h, diluted with water (50 mL) and neutralized with Na2CO3 (pH˜8). The neutralized mixture was extracted with EtOAc (3×50 mL), the combined extract was washed with water and brine, and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified on HPLC to give 0.62 g (48%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.81 (broad s, 1H), 7.68-7.73 (m, 1H), 7.57-7.62 (m, 1H), 7.39 (t, J=8.0 Hz, 1H), 2.64 (q, J=8.0 Hz, 2H), 2.00 (s, 3H), 1.10 (t, J=8.0 Hz, 3H).

Aufarbeitung

  1. extractionThe neutralized mixture was extracted with EtOAc (3×50 mL)
  2. extractionthe combined extract
  3. washwas washed with water and brine
  4. dry with materialdried with anhydrous MgSO4
  5. customThe filtrate was evaporated
  6. customthe residue was purified on HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a6b3bc18edfe4035bedbd1b424ea7342
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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