Potassium Cyanide → 3-Cyano-5-nitrobenzoic acid

HRID 341884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341884
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].[C-:24]#[N:25].[K+]>Cl.O>[C:24]([C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6])#[N:25]

Komponenten

7

Edukt 4

HCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 2393423-Amino-5-nitrobenzoic acidHCID 23668193Sodium Nitrite

Produkt 1

HCID 219425653-Cyano-5-nitrobenzoic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel4×

Versuchsvorschrift

3-Amino-5-nitrobenzoic acid (3.64 g, 20 mM) was dissolved in concentrated hydrochloric acid (20 ml), diluted with water (75 ml), cooled to 0°, and added over 30 minutes to a solution of NaNO2 (1.38 g, 20 mM) in water (10 ml). The pH was adjusted to 6.2 with saturated Na2CO3 solution. A mixture of CuSO4.5H2O (10 g, 42 mM) in water (40 ml) and KCN (10 g, 154 mM) in water (20 ml) was heated to 65°, the solution of diazonium salt added over 15 minutes, and the mixture refluxed for 40 minutes. After cooling, and acidifying with 2M hydrochloric acid, the organics were extracted into ethyl acetate (2×200 ml). The combined extracts were washed with aqueous NaH2PO4, water, brine, and dried over Na2SO4. Evaporation gave 3-cyano-5-nitrobenzoic acid (3.6 g, 94%).

Aufarbeitung

  1. temperaturecooled to 0°
  2. temperaturewas heated to 65°
  3. temperaturethe mixture refluxed for 40 minutes
  4. temperatureAfter cooling
  5. extractionthe organics were extracted into ethyl acetate (2×200 ml)
  6. washThe combined extracts were washed with aqueous NaH2PO4, water, brine
  7. dry with materialdried over Na2SO4
  8. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-8bef02863209431e9939890ea6f6bf33
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856321

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