4-Aminobenzoic Acid → 4-(1-Cyanocyclobutylamino)benzoic acid

HRID 245017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245017
[C-:1]#[N:2].[Na+].[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.[C:14]1(=O)[CH2:17][CH2:16][CH2:15]1>C(O)(=O)C>[C:1]([C:14]1([NH:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[CH2:17][CH2:16][CH2:15]1)#[N:2]

Komponenten

5

Edukt 3

HCID 9784-Aminobenzoic AcidHCID 8929Sodium CyanideHCID 14496Cyclobutanone

Produkt 1

HCID 671321724-(1-Cyanocyclobutylamino)benzoic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Sodium cyanide (0.245 g, 5 mmol) was added to a mixture of 4-aminobenzoic acid (0.274 g, 2 mmol) and cyclobutanone (0.21 g, 3 mmol) in 90% acetic acid (4.5 ml). The reaction mixture was stirred at room temperature for 15 hours. The mixture was washed with aqueous HCl (pH 2) and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to dryness under vacuum to yield 4-(1-cyanocyclobutylamino)benzoic acid (51a) (0.426 g, 1.97 mmol, 99%) as a white solid.

Aufarbeitung

  1. washThe mixture was washed with aqueous HCl (pH 2)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-823cb04dd01043e3a58b15491c78df16
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658681B2

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