1-[2-Nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehyde → Ethyl 10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine-7-carboxylate

HRID 3603

Reaction equation

HRID 3603 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=O)([O-])=O.[H][H]>C(O)C.[Pd]>[CH:9]1[CH:10]=[CH:11][N:7]2[CH2:6][C:5]3[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=[CH:17][C:4]=3[NH:1][CH2:12][C:8]=12

Participants

5

Reactant 2

HCID 218371151-[2-Nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 21837067Ethyl 10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine-7-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.0 g of 1-[2-nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehyde in 150 ml of absolute ethanol containing 1.0 g of 10% Pd/c is hydrogenated in a Parr apparatus for 16 hours under 40 psi of hydrogen. The reaction mixture is filtered through a pad of diatomaceous earth and the filtrate concentrated in vacuo to a residue of 5.5 g of the desired product as a solid; mass spectrum (M+H)255.

Workup

  1. filtrationThe reaction mixture is filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo to a residue of 5.5 g of the desired product as a solid

Sources & evidence

ORD record
ord-3632dee499a345c98f0a864a80748938
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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