Nitrogen → 4-Cyano-2-ethoxybenzoic acid

HRID 1005926

Reaktionsgleichung

Reaktionsgleichung von HRID 1005926
[C:1]([Cu])#[N:2].[C-]#N.[Na+].[CH2:7]([O:9][C:10]1[CH:18]=[C:17](N)[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])[CH3:8].N([O-])=O.[Na+].[C-]#N.[Na+].C([Cu])#N.N#N>O.Cl.C(O)CCCCCCC>[CH2:7]([O:9][C:10]1[CH:18]=[C:17]([C:1]#[N:2])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])[CH3:8]

Komponenten

10

Edukt 6

HCID 947NitrogenHCID 8929Sodium CyanideHCID 101763852-Ethoxy-4-aminobenzoic acidHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, Verbindung2×HCID 178511486HCID 178511486, Verbindung

Produkt 1

HCID 226750384-Cyano-2-ethoxybenzoic acidAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9571-OctanolKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

In a 1 l reactor equipped with a sealed mechanical stirrer, CuCN (12 g, 134 mmol) were suspended in 100 ml of distilled water. NaCN (18.3 g, 373 mmol) was added with vigorous stirring and the internal temperature was kept below 40° C. until all the CuCN went into solution. The suspension of 2-ethoxy-4-aminobenzoic acid (20 g, 110 mmol) in water (200 ml) and concentrated HCl (33 ml) was stirred and cooled in an ice bath. When the temperature reached 5° C., a solution of NaNO2 (9.7 g, 140 mmol) in water (30 ml) was added dropwise at such a rate as to maintain the temperature below 5° C. When all the NaNO was added, the solution was slowly introduced through an ice cooled dropping funnel into the reactor containing the NaCN/CuCN solution. A reaction took place with the vigorous formation of N2. A few drops of octanol were added to keep the foaming under control. Stirring was continued for 4 h. The resulting suspension was then extracted with ethyl acetate (3×100 ml) and the organic phase dried over MgSO4 and evaporated under vacuum obtaining 15 g of the title compound (yield 71.1%) as a light brown powder, mp=170-172° C.

Aufarbeitung

  1. customIn a 1 l reactor equipped with a sealed mechanical stirrer
  2. customwas kept below 40° C. until all
  3. stirringwas stirred
  4. temperaturecooled in an ice bath
  5. customreached 5° C.
  6. temperatureto maintain the temperature below 5° C
  7. temperaturecooled
  8. stirringStirring
  9. extractionThe resulting suspension was then extracted with ethyl acetate (3×100 ml)
  10. dry with materialthe organic phase dried over MgSO4
  11. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a356f1e0bf994f0e8f48d5f57113b302
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787550B1

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