Ethylene Glycol → 6-Nitro-1,2-dihydroisoquinolin-1-one

HRID 708797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 708797
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7](OC)=[O:8].N.C(O)CO>>[N+:15]([C:13]1[CH:14]=[C:5]2[C:6](=[CH:11][CH:12]=1)[C:7](=[O:8])[NH:2][CH:3]=[CH:4]2)([O-:17])=[O:16]

Komponenten

4

Edukt 3

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 87664981(E)-Methyl 2-(2-(dimethylamino)vinyl)-4-nitrobenzoate

Produkt 1

HCID 707009796-Nitro-1,2-dihydroisoquinolin-1-oneAusbeute 85 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To Intermediate 3B (1.54 g, 6.15 mmol) in a microwave tube was added 8.0 N ammonia in ethylene glycol (7.69 mL, 61.5 mmol). The tube was placed in microwave and heated at 140° C. for 30 min. The reaction mixture was triturated with EtOAc, stored at 0° C. over night. The precipitate was collected to give Intermediate 3C (0.995 g, 5.23 mmol, 85% yield) as a brown solid. The filtrate was washed with water. The organic layer was dried over sodium sulfate. After evaporation of solvent, the crude was triturated with EtOAc to give additional product. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.35 (br. s., 1H) 8.63 (d, J=2.20 Hz, 1H) 8.39 (d, J=8.79 Hz, 1H) 8.19 (dd, J=8.79, 2.20 Hz, 1H) 7.36 (d, J=7.03 Hz, 1H) 6.82 (d, 1H); MS (ESI) m/z: 191.1 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was triturated with EtOAc
  2. waitstored at 0° C. over night
  3. customThe precipitate was collected

Quellen und Nachweise

ORD-Eintrag
ord-233ece1c319746318debc57332713bfd
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174974B2

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