1-(2-nitrobenzyl)-1H-pyrrole-2-carbaldehyde → 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

HRID 3505ノート

反応式

HRID 3505 の反応式
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=O)([O-])=O>C(OCC)(=O)C.C(O)C.C(Cl)Cl.[Pd]>[CH:9]1[CH:10]=[CH:11][N:7]2[CH2:6][C:5]3[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=3[NH:1][CH2:12][C:8]=12

参加物

6

反応物 1

HCID 7362171-(2-nitrobenzyl)-1H-pyrrole-2-carbaldehyde

生成物 1

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine収率 66.6%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 30.6 g of 1-(2-nitrobenzyl)-2-pyrrolecarboxaldehyde and 3.06 g of 10% Pd/C in 400 ml of ethyl acetate and 400 ml of ethyl alcohol is hydrogenated over 18 hours. The reaction mixture is filtered through diatomaceous earth and the filtrate is treated with activated carbon and filtered through diatomaceous earth. The filtrate is concentrated in vacuo to give a residue which is dissolved in methylene chloride containing ethyl alcohol. The solution is passed through a pad of silica gel and the pad washed with a 7:1 hexane-ethyl acetate solution to give 16.31 g of the desired product as solid, m.p. 145°-148° C.

後処理

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. additionthe filtrate is treated with activated carbon
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto give a residue which
  6. washthe pad washed with a 7:1 hexane-ethyl acetate solution

出典と根拠

ORDレコード
ord-6cf1c224c2e047dda0712160d1f7fd19
出典データセット
uspto-grants-1998_03
特許番号
US05733905

反応ノート

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