Hydrazine → 10,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 3506

Reaktionsgleichung

Reaktionsgleichung von HRID 3506
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 9321HydrazineHCID 1064038210,11-dihydro-10(4-nitrobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 21.58 g of 10,11-dihydro-10-(4-nitrobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 325 ml of ethyl alcohol is added 2.15 g of 10% Pd/C and 5.16 g of hydrazine followed by stirring and heating under reflux for 15 hours. The room temperature reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a solid which is dissolved in methylene chloride and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give 19.2 g of the desired product as a tan solid. The solid is purified by flash chromatography using 7:1 ethyl acetate-hexane to give 17.97 g of the desired product, m.p. 166°-168° C.

Aufarbeitung

  1. temperatureheating
  2. temperatureunder reflux for 15 hours
  3. customThe room temperature reaction mixture
  4. filtrationis filtered through diatomaceous earth
  5. concentrationThe filtrate is concentrated in vacuo to a solid which
  6. dissolutionis dissolved in methylene chloride
  7. concentrationThe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2c3b42b17a5748819721657743389fb5
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

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