Glycine → Glycine, N-(4-nitrophenyl)-

HRID 1910767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910767
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].F[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1)([O-:15])=[O:14]

Komponenten

6

Edukt 3

HCID 750GlycineHCID 9590p-FluoronitrobenzeneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 12095Glycine, N-(4-nitrophenyl)-Ausbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Glycine (5.31 g, 70.8 mmol) was added to a mixture of 1-fluoro-4-nitro-benzene (5.0 g, 35.4 mmol) and sodium bicarbonate (5.94 g, 70.8 mmol) in dioxane (10 mL) and water (60 mL) and heated at reflux for 6 h. The reaction mixture was cooled to room temperature and washed with ethyl acetate. The aqueous layer was acidified with 1N hydrochloric acid to pH ˜3 and extracted with ethyl acetate. The extract was washed with water, brine, dried over anhydrous sodium sulfate and concentrated to dryness to afford (4-nitro-phenylamino)-acetic acid (5.0 g, 72%) as a yellow solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 6 h
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8b8eb3a99a7d4c0fbbf264e0ef371745
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604029B2

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