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 1903628ノート

反応式

HRID 1903628 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-36d9215cabbe444aa8773265c9372497
出典データセット
uspto-grants-1984_03
特許番号
US04436662

反応ノート

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