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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2421576Erstellt: 25. Oktober 2026

Phosphoric Acid → 5-chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

https://huagongshe.com/reaction/2421576

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPhosphoric AcidHCID 1004—
EduktPhosphorus oxide (P4O10)HCID 14812—
Edukt3-(2-(4-Chlorophenoxy)phenyl)-1-methylpyrrolidine-2,4-dioneHCID 23148658—
LösungsmittelWaterHCID 962—
Produkt5-chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-oneHCID 5872918358%

Reaktionsschritte

P2O5 (90 grams) was added in portions to H3PO4 (90 grams) while maintaining the temperature below 140° C. The mixture was heated at 115° C. for 1.5 hour, whereupon 3-[2-(4-chloro-phenoxy)-phenyl]-1-methyl-pyrrolidine-2,4-dione (XI) (30 grams; 95 mmol) was added. The resulting mixture was stirred for 4 days at 115° C. to 130° C. with extra P2O5 (in total 5 portions of 5 grams each were added). The mixture was poured into water (200 ml) and the resulting precipitate was stirred overnight. The mixture was extracted with dichloromethane (250 ml) and washed with sat. NaHCO3 (pH=7). After drying on magnesium sulphate the solvent was removed under vacuum. The resulting crude product was dissolved in methanol (520 ml) at 70° C. Following removal of part of the methanol by evaporation the product crystallized. The mixture was stirred overnight at −12° C. The crystals were filtered and dried to provide 5-chloro-2,3-dihydro-2-methyl-1H-dibenz[2,3;6,7]oxepino[4,5-c]pyrrol-1-one (VI) (16.4 grams, 55 mmol; 58%), purity according to GC 92%. 1H-NMR (400 MHz, CDCl3): 3.2 (s, 3H), 4.3 (s, 1H), 3.8 (m, 1H), 7.2-7.4 (m, 6H), 8.2 (dd, 1H).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07956202B2
Quelldatensatzuspto-grants-2011_06
ORD IDord-9f8580329ade408bad8b536f504fa700
Quellennotizuspto-grants-2011_06