Nitrazepam → 2-Amino-2'-[alpha-(hydroxyimino)benzyl]-4'-nitro-acetanilide

HRID 2418314

Reaktionsgleichung

Reaktionsgleichung von HRID 2418314
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1)([O-:3])=[O:2].Cl.[NH2:23][OH:24]>N1C=CC=CC=1.C(Cl)Cl>[NH2:10][CH2:11][C:12]([NH:13][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:21][C:8]=1[C:9](=[N:23][OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]

Komponenten

5

Edukt 2

HCID 4506NitrazepamHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 867396452-Amino-2'-[alpha-(hydroxyimino)benzyl]-4'-nitro-acetanilide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 10 g (35.55 mmol) of 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one and 3.7 g (53.3 mmol) of hydroxylamine hydrochloride in 80 ml of pyridine is heated under reflux for 1 hour. After cooling, the mixture is taken up in methylene chloride, washed with water, dried and evaporated. The residual pyridine is removed in vacuo azeotropically with toluene. The solid crude product is suspended in hot tert.-butyl methyl ether and filtered off. There is obtained 2-amino-2'-[α-(hydroxyimino)-benzyl]-4'-nitro-acetanilide of melting point 167° (decomposition).

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter cooling
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residual pyridine is removed in vacuo azeotropically with toluene
  7. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-c547788ae59b419babdca8db616cd6d3
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04472435

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