Quinoline → 4-Cyano-3-nitrobenzoic acid

HRID 635404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 635404
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[N:14]1C2C(=CC=CC=2)C=C[CH:15]=1>Cl.O>[C:15]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])#[N:14]

Komponenten

5

Edukt 2

HCID 7047QuinolineHCID 73204-Chloro-3-nitrobenzoic acid

Produkt 1

HCID 221685834-Cyano-3-nitrobenzoic acidAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Chloro-3-nitrobenzoic acid (5.84 g, 29 mM), cuprous cyanide (5.2 g, 58 mM), cuprous chloride (0.96 g, 9.7 mM), and quinoline (6.9 ml, 58 mM) were heated under an argon atmosphere at 180′ for 3.5 hours. After cooling, the mixture was dissolved in concentrated hydrochloric acid (60 ml), diluted with water (80 ml), and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with aqueous NaH2PO4, brine, and dried over MgSO4. Crude product was purified by chromatography on silica, eluting with a mixture of dichloromethane/acetic acid (98:2), to give 4-cyano-3-nitrobenzoic acid (2.65 g, 48%). Nmr (DMSO-d6): δ 8.31 (d, 1H); 8.41 (dd, 1H); 8.68 (d, 1H).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with aqueous NaH2PO4, brine
  4. dry with materialdried over MgSO4
  5. customCrude product was purified by chromatography on silica
  6. washeluting with a mixture of dichloromethane/acetic acid (98:2)

Quellen und Nachweise

ORD-Eintrag
ord-660b76d2086a48daa88d3e5853a7cc92
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187804B1

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