methyl 2-[2-methyl-1-(4-nitrobenzyl)-1H-indol-3-yl]acetate → methyl 2-[1-(4-aminobenzyl)-2-methyl-1H-indol-3-yl]acetate

HRID 589333Notes

Reaction equation

HRID 589333 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2>CO.[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:2]2[CH3:1])=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 89590250methyl 2-[2-methyl-1-(4-nitrobenzyl)-1H-indol-3-yl]acetate

Product 1

HCID 89590248methyl 2-[1-(4-aminobenzyl)-2-methyl-1H-indol-3-yl]acetateYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a dry reaction vessel, methyl 2-[2-methyl-1-(4-nitrobenzyl)-1H-indol-3-yl]acetate (300 mg, 0.887 mmol) was added, and dissolved in 10 mL methanol. 10% Pd/C 20 mg was added, and reacted under hydrogen for 3 hours. After completion of the reaction, it was filtered. The filter cake was washed with methanol, and the filtrate was rotate evaporated to dryness to obtain a solid 260 mg, at a yield of 95.0%.

Workup

  1. additionwas added
  2. customreacted under hydrogen for 3 hours
  3. customAfter completion of the reaction, it
  4. filtrationwas filtered
  5. washThe filter cake was washed with methanol
  6. customthe filtrate was rotate evaporated to dryness

Sources & evidence

ORD record
ord-c1ac13c4cb204352ba7bba8dbbb77727
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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