Ethyl Acetate → 10,11-Dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c]-[1,4]benzodiazepine

HRID 3523

Reaction equation

HRID 3523 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][N:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][N:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2183701510,11,Dihydro-10-(4-nitrobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepineHCID 178418361HCID 178418361, compound

Product 1

HCID 2183708710,11-Dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c]-[1,4]benzodiazepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5 mmol of 10,11-dihydro-10-(4-nitrobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 10 ml of ethyl alcohol and 10 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours in a Parr hydrogenator at 35 psi of hydrogen. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a solid which is purified by flash chromatography to give the desired product.

Workup

  1. filtrationThe reaction mixture is filtered through a pad of diatomaceous earth
  2. concentrationThe filtrate is concentrated in vacuo to a solid which
  3. customis purified by flash chromatography

Sources & evidence

ORD record
ord-9b7f8c988c1346ab89148d00d0ed8b57
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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