Quinoline → 4-Cyano-3-nitrobenzoic acid

HRID 1059740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059740
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-3d0fcc3d44aa4ba2984f64d0c45eb787
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521612B2

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