(E)-methyl 4-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate → Methyl 4-amino-1H-indole-6-carboxylate

HRID 852598Notes

Reaction equation

HRID 852598 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:14]([N+:15]([O-])=O)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:18]([O-])=O>CO.[Pd]>[NH2:15][C:14]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]=[C:6]2[C:5]=1[CH:4]=[CH:3][NH:18]2

Participants

4

Reactant 1

HCID 11587426(E)-methyl 4-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate

Product 1

HCID 14243967Methyl 4-amino-1H-indole-6-carboxylateYield 77.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[(E)-2-(dimethylamino)ethenyl]-3,5-dinitrobenzoate (D200) (10 g, 34 mmol, 1 equiv) in MeOH (250 ml) was added 10% palladium on charcoal (50% wet, 1.0 g, 5% w/w) and the resulting mixture was stirred under an atmosphere of hydrogen for 7 h. The catalyst was removed by filtration through a pad of celite and the solution concentrated in vacuo. The residue was triturated with AcOEt/iso-hexane to give methyl 4-amino-1H-indole-6-carboxylate (D201) (5 g, 77%) as a dark pink solid. [M+H]+=191.0, RT=1.20 min.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. concentrationthe solution concentrated in vacuo
  3. customThe residue was triturated with AcOEt/iso-hexane

Sources & evidence

ORD record
ord-cd997909bb2f4fadb1aa56291c69be37
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…