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

HRID 1739965Notes

Reaction equation

HRID 1739965 reaction equation
[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

Participants

6

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ef81d9eeba5849688dac636acc6436c4
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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