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

HRID 975855Notes

Reaction equation

HRID 975855 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 hexaneethyl 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 hexaneethyl acetate solution

Sources & evidence

ORD record
ord-72c50703ae99490eaa7cccf12de1693f
Source dataset
uspto-grants-1997_03
Patent number
US05610156

Reaction notes

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