Benzoic acid, 3-[(1E)-2-(dimethylamino)ethenyl]-2-nitro-, methyl ester → Methyl indole-7-carboxylate

HRID 1198532Notes

Reaction equation

HRID 1198532 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:6]([N+:15]([O-])=O)=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9].[H][H]>C1(C)C=CC=CC=1.[Pd]>[NH:15]1[C:6]2[C:5](=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]([O:10][CH3:11])=[O:9])[CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 771483Benzoic acid, 3-[(1E)-2-(dimethylamino)ethenyl]-2-nitro-, methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 676694Methyl indole-7-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of methyl 3-[2-(E)-(dimethylamino)ethenyl]-2-nitrobenzoate (12.0 g, 48 mmol) in toluene (200 ml) was hydrogenated at 60 psi over 10% palladium on charcoal (1.5 g) until hydrogen uptake ceased. The catalyst was filtered off, the filtrate was evaporated and the residue was chromatographed on silica to give the product.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customthe residue was chromatographed on silica
  4. customto give the product

Sources & evidence

ORD record
ord-6feaadd5da724c1ebd30712baed05f8f
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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