N-Aminophthalimide → 2-[2-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione

HRID 1796962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796962
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([CH3:14])[CH2:11][CH:12]=O)=[C:5]([CH3:16])[CH:4]=1.[NH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>Cl.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([N:18]3[C:22](=[O:23])[C:21]4[C:20](=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:19]3=[O:28])[CH:12]=[CH:11][C:10]=2[CH3:14])=[C:5]([CH3:16])[CH:4]=1

Komponenten

5

Edukt 2

HCID 74645N-AminophthalimideHCID 221747894-(4-Methoxy-2-methylphenyl)-3-methyl-4-oxobutanal

Produkt 1

HCID 221747872-[2-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dioneAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of the 4-(4-methoxy-2-methylphenyl)-3-methyl-4-oxobutanal (0.31 g, 1.40 mmol) and N-aminophthalimide (0.28 g, 1.55 mmol) in HCl (5N, 0.15 mL) and dioxane (10.0 mL) was refluxed for 2 h. After cooling down to room temperature, the mixture was concentrated in vacuo and the residue was subjected to column chromatography (silica gel, 1/9 EtOAc/heptane) to give 0.42 g (86%) of pale yellow solid as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.91–7.89 (m, 1H), 7.81–7.73 (m, 3H), 7.09 (d, J=8 Hz, 1H), 6.74–6.72 (m, 2H), 6.58 (dd, J=3, 8 Hz, 1H), 6.29 (s, 1H), 3.73 (s, 3H), 2.23 (s, 3H), 1.97 (s, 3H); MS m/z 347.1 (M++H).

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. concentrationthe mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6e52bbaa8894a2ba03b6a2ac29b6791
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034023B2

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