Acetic Acid → 2,3-dimethoxy-6,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 2215130Notes

Reaction equation

HRID 2215130 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][N:12]2[CH:16]=[CH:15][CH:14]=[C:13]2[CH:17]=O)=[C:5]([N+:19]([O-])=O)[CH:4]=1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>[Pd].C(OCC)(=O)C>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[NH:19][CH2:17][C:13]3=[CH:14][CH:15]=[CH:16][N:12]3[CH2:11][C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 3108271-[(4,5-Dimethoxy-2-nitrophenyl)methyl]-1H-pyrrole-2-carboxaldehyde

Product 1

HCID 3108382,3-dimethoxy-6,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 76.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the 1-[(4,5-dimethoxy-2-nitrophenyl)methyl]-1H-pyrrole-2-carboxaldehyde of Step A (4.97 g), acetic acid (0.5 mL), magnesium sulfate (0.5 g) and 10% palladium on charcoal (0.5 g) in ethyl acetate (50 mL) was hydrogenated overnight at atmospheric pressure. The reaction was then filtered through Celite and the solvent removed in vacuo to give the crude title compound as an amber foam (3.2 g) which was used in the next step without further purification.

Workup

  1. filtrationThe reaction was then filtered through Celite
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a03c0895d4f1416db47ff3ec81e1d090
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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