3-[1-(4-nitrobenzyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethyl propanoic acid → 3-[1-(4-aminobenzyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethyl propanoic acid

HRID 1090207Notes

Reaction equation

HRID 1090207 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[C:11]([CH3:20])=[C:10]2[CH2:21][C:22]([CH3:27])([CH3:26])[C:23]([OH:25])=[O:24])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[C:11]([CH3:20])=[C:10]2[CH2:21][C:22]([CH3:26])([CH3:27])[C:23]([OH:25])=[O:24])=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 156788113-[1-(4-nitrobenzyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethyl propanoic acid

Product 1

HCID 156788123-[1-(4-aminobenzyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethyl propanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

500 mg of the product of Step 1 was dissolved in 35 ml of absolute ethanol and 50 mg of 10% palladium on carbon catalyst added. The suspension was hydrogenated at 50 psi until consumption of 2 mole equivalents of hydrogen occurred. The catalyst was removed by filtration and the title compound was isolated by vacuum distilation of the solvent (489 mg).

Workup

  1. customThe suspension was hydrogenated at 50 psi until consumption of 2 mole equivalents of hydrogen
  2. customThe catalyst was removed by filtration

Sources & evidence

ORD record
ord-9dec003db0c04a34937d81991e63c98d
Source dataset
uspto-grants-1992_01
Patent number
US05081145

Reaction notes

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