4-[2-(2-chlorobenzoyl)-4-chlorophenyl]-5-ethyl-1H-pyrrole-3-carbonitrile → 8-chloro-6-(2-chlorophenyl)-1-ethyl-2H,4H-pyrrolo[3,4-d][2]benzazepine

HRID 1903628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903628
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[C:13]1[C:14]([C:20]#[N:21])=[CH:15][NH:16][C:17]=1[CH2:18][CH3:19])=O>[Ni].C(O)(=O)C>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]2[C:13]3[C:14](=[CH:15][NH:16][C:17]=3[CH2:18][CH3:19])[CH2:20][N:21]=[C:4]([C:3]3[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=3[Cl:1])[C:6]=2[CH:11]=1

Komponenten

4

Edukt 1

HCID 132809324-[2-(2-chlorobenzoyl)-4-chlorophenyl]-5-ethyl-1H-pyrrole-3-carbonitrile

Produkt 1

HCID 132809348-chloro-6-(2-chlorophenyl)-1-ethyl-2H,4H-pyrrolo[3,4-d][2]benzazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3.3 g (8.9 mmol) of 4-[2-(2-chlorobenzoyl)-4-chlorophenyl]-5-ethyl-1H-pyrrole-3-carbonitrile, 0.5 teaspoon of Raney nickel, and 100 ml of acetic acid was hydrogenated on a Parr apparatus at 50 psi for 16 hours. The Raney nickel was removed by filtration through a pad of Celite, and the filtrate was concentrated at reduced pressure to a dark residue. The residue was partitioned between ice water and ether and basified with concentrated ammonium hydroxide solution. The ether was removed at reduced pressure, and the aqueous residue was stirred for 1 hour. The resulting precipitate was collected by filtration and dissolved in tetrahydrofuran. The tetrahydrofuran solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to a residue which crystallized from ether to give 8-chloro-6-(2-chlorophenyl)-1-ethyl-2H,4H-pyrrolo[3,4-d][2]benzazepine as yellow prisms, mp 251°-253° C. Recrystallization from a mixture of ether and methylene chloride gave off-white prisms, mp 254° -255° C.

Aufarbeitung

  1. customThe Raney nickel was removed by filtration through a pad of Celite
  2. concentrationthe filtrate was concentrated at reduced pressure to a dark residue
  3. customThe residue was partitioned between ice water and ether and basified with concentrated ammonium hydroxide solution
  4. customThe ether was removed at reduced pressure
  5. filtrationThe resulting precipitate was collected by filtration
  6. dissolutiondissolved in tetrahydrofuran
  7. dry with materialThe tetrahydrofuran solution was dried over anhydrous sodium sulfate
  8. concentrationconcentrated at reduced pressure to a residue which
  9. customcrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-36d9215cabbe444aa8773265c9372497
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436662

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