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

HRID 440735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 440735
[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

Komponenten

6

Edukt 1

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

Produkt 1

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7290e85e3517415b86b1117e85dd5561
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521173

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