3,4-Dimethoxybenzeneacetonitrile → 2,3-dihydro-6,7-dimethoxyspiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione

HRID 1287857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1287857
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)([CH2:10][CH2:11][C:12]([O:14]C)=O)[CH2:4][CH2:5][C:6]([O:8]C)=O)#[N:2].C[O:27]C1C=C(CC#N)C=CC=1OC>>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:24][CH3:25])[C:3]1([CH2:10][CH2:11][C:12](=[O:14])[NH:2][C:1]1=[O:27])[CH2:4][CH2:5][C:6]2=[O:8]

Komponenten

3

Edukt 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 1803855Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate

Produkt 1

HCID 215067812,3-dihydro-6,7-dimethoxyspiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trioneAusbeute 18 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Unpurified dimethyl γ-cyano-γ-(3,4-dimethoxyphenyl)pimelate, prepared from 334 grams of 3,4-dimethoxyphenylacetonitrile as described by Horning et al., J. Am. Chem. Soc., 74, 773 (1942), was added with stirring to 3.0 kg of polyphosphoric acid. This reaction mixture was stirred at 110° C. for 2 hours and poured into 6.0 liters of crushed ice with stirring. The resulting solid was filtered and recrystallized from isopropyl alcohol-water to give 65.8 grams (18%) of 2,3-dihydro-6,7-dimethoxyspiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione, melting point 269°-271° C.

Aufarbeitung

  1. addition, 74, 773 (1942), was added
  2. stirringwith stirring
  3. filtrationThe resulting solid was filtered
  4. customrecrystallized from isopropyl alcohol-water

Quellen und Nachweise

ORD-Eintrag
ord-615754386bef4a4399f91feb0d0c42a6
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03985888

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