N-(2-nitrobenzoyl)pyrrole-2-carboxaldehyde → 10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

HRID 3499

Reaction equation

HRID 3499 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=O)=[O:7])([O-])=O>C(OCC)(=O)C.Cl.[Pd]>[CH:10]1[CH:11]=[CH:12][N:8]2[C:6](=[O:7])[C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[NH:1][CH2:13][C:9]=12

Participants

5

Reactant 1

HCID 21837074N-(2-nitrobenzoyl)pyrrole-2-carboxaldehyde

Product 1

HCID 2183707610,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-oneYield 82.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.5 g of N-(2-nitrobenzoyl)pyrrole-2-carboxaldehyde in 50 ml of ethyl acetate, 2 drops of concentrated HCl and 0.3 g of 10% Pd/C is shaken in a Parr apparatus under hydrogen pressure for 1.75 hours. The mixture is filtered, 0.4 g of 10% Pd/C added and the mixture shaken in a Parr apparatus under hydrogen pressure for 2 hours. The reaction mixture is filtered through diatomaceous earth and the filtrate concentrated in vacuo to give 1.0 g of a yellow oil. The residue is purified on thick layer chromatography plates by elution with 4:1 ethyl acetate:hexane to give 107 mg of the desired product as an oily solid.

Workup

  1. filtrationThe mixture is filtered
  2. addition0.4 g of 10% Pd/C added
  3. stirringthe mixture shaken in a Parr apparatus under hydrogen pressure for 2 hours
  4. filtrationThe reaction mixture is filtered through diatomaceous earth
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-3085189734d041b78484ffa27fd0825c
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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