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

HRID 14168Notes

Reaction equation

HRID 14168 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>C(OCC)(=O)C.[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-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 4-[(E)-2-(dimethylamino)ethenyl]-3,5-dinitrobenzoate (19.3 g) in ethyl acetate (200 mL) was added 5% palladium on carbon (1.5 g). The mixture was placed under 45 PSI H2 and shaken overnight. The mixture was filtered through celite and concentrated. The residue was dissolved in CH2Cl2 to which was added ((1:1) H2O:conc. HCl (250 mL)). The resulting solids were collected by filtration, dissolved in ethyl acetate and washed with 2N NaOH. The ethyl acetate layer with anhydrous magnesium sulfate, filtered and concentrated to give 7.4 g if the title compound: 1H NMR (CDCl3) δ 3.91, 4.01, 6.51, 7.09, 7.27, 8.40.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2 to which
  4. additionwas added ((1:1) H2O:conc. HCl (250 mL))
  5. filtrationThe resulting solids were collected by filtration
  6. dissolutiondissolved in ethyl acetate
  7. washwashed with 2N NaOH
  8. filtrationThe ethyl acetate layer with anhydrous magnesium sulfate, filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2e4e8db5af7b465e9425cc733d2ab4a9
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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