Maleic Anhydride → 1-Naphthalenecarbonitrile

HRID 723659

Reaktionsgleichung

Reaktionsgleichung von HRID 723659
N[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[CH:4][CH:3]=1.C1(=O)OC(=O)C=C1>CC(O)=O>[C:5]1([C:12]#[N:13])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 7923Maleic AnhydrideHCID 428284-Amino-1-naphthalenecarbonitrile

Produkt 1

HCID 68461-Naphthalenecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 4-amino-1-naphthalenecarbonitrile (19.2 g, 114 mmol) and maleic anhydride (14.0 g, 113 mmol) in AcOH (230 mL) was heated at 115° C. for 12 h. After cooling to rt, the reaction mixture was concentrated under reduced pressure then diluted with CH2Cl2 (2.5 L). The organic layer was washed 3× with H2O (3 L), 1× with sat. aq. Na2CO8 (1 L) and 1× with brine (1 L), dried over MgSO4 and concentrated to −200 mL under reduced pressure. Purification by flash chromatography on cation exchange resin (60 g, CUBX13M6 from United Chemical Technologies) eluting with CH2Cl2 gave 25.0 g (88%) of 4-(2,5-dihydro-2,5-dioxo-1H-1-yl)]-naphthalenecarbonitrile as a yellow solid. HPLC: 96% at 2.48 min (retention time) (Phenomenex-prime S5-C18 column 4.6×50 mm, 10–90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 249.25 [M+H]+.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionthen diluted with CH2Cl2 (2.5 L)
  3. washThe organic layer was washed 3× with H2O (3 L), 1× with sat. aq. Na2CO8 (1 L) and 1× with brine (1 L)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to −200 mL under reduced pressure
  6. customPurification by flash chromatography on cation exchange resin (60 g, CUBX13M6 from United Chemical Technologies)
  7. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-2ca1479167d844b3ac63d3cdd9910f99
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141578B2

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