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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1764719Erstellt: 25. Oktober 2026

Acetone Cyanohydrin → 3-nitro-5-oxo-6,7,8,9-tetrahydro [5H] benzocycloheptene-7-carbonitrile

https://huagongshe.com/reaction/1764719

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktAcetone CyanohydrinHCID 6406—
Edukt8,9-dihydro-3-nitro-5H-benzocyclohepten-5-oneHCID 20094732—
Produkt3-nitro-5-oxo-6,7,8,9-tetrahydro [5H] benzocycloheptene-7-carbonitrileHCID 54523296—

Reaktionsschritte

The novel process of the invention for the preparation of a compound of formula I wherein X is nitro comprises reacting 3-nitro-8,9-dihydro [5H] benzocycloheptene-5-one of the formula ##STR3## with acetone cyanhydrin of the formula to obtain 3-nitro-5-oxo-6,7,8,9-tetrahydro [5H] benzocycloheptene-7-carbonitrile of the formula ##STR4## reducing the latter with diborane in an organic solvent to obtain 3-nitro-7-aminomethyl-6,7,8,9-tetrahydro [5H] benzocycloheptene-5-ol of the formula ##STR5## deshydrating the latter to form 2-nitro-6,7-dihydro [5H] benzocycloheptene-7-methanamine of the formula ##STR6## and either reacting the latter with formic aldehyde and sodium cyanoborohydride to obtain N,N-dimethyl-2-nitro-6,7-dihydro [5H] benzocycloheptene 7-methanamine of the formula ##STR7## which may be reacted with an alkyl chloroformate of the formula

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS04117164
Quelldatensatzuspto-grants-1978_09
ORD IDord-5f28c8fa63124e45bd3c38950184f27f
Quellennotizuspto-grants-1978_09