Phthalimide → 2-(Quinolin-6-ylmethyl)isoindoline-1,3-dione

HRID 456048

Reaktionsgleichung

Reaktionsgleichung von HRID 456048
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:31]1[C:40]2[C:35](=[CH:36][C:37]([CH2:41]O)=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1COCC1>[N:31]1[C:40]2[C:35](=[CH:36][C:37]([CH2:41][N:2]3[C:3](=[O:10])[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:1]3=[O:11])=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 15143856-HydroxymethylquinolineHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 230792942-(Quinolin-6-ylmethyl)isoindoline-1,3-dioneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a solution of isoindoline-1,3-dione (6.47 g, 44.0 mmol) and triphenylphosphine (11.53 g, 44.0 mmol) in THF (70 mL) at a 0° C., was added a solution of quinolin-6-ylmethanol (7 g, 44.0 mmol) in THF (30 mL) and (E)-diisopropyl diazene-1,2-dicarboxylate (8.89 g, 44.0 mmol) dropwise over a period of 30 min. The mixture was then heated to 30° C. for 20 h. The reaction was cooled to rt and concentrated in vacuo. The resulting residue was purified by Analogix silica gel with gradient hexanes:EtOAc to provide 2-(quinolin-6-ylmethyl)isoindoline-1,3-dione (12.04 g) in 95% yield. LCMS (method A): [MH]+=2.99, tR=4.89 min.

Aufarbeitung

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by Analogix silica gel with gradient hexanes

Quellen und Nachweise

ORD-Eintrag
ord-07d2e366b8cb4d7d8dd2f7f1f447e29b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

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