5-Nitro-3-(2-nitropropyl)indole → 5-Amino-3-(2-nitropropyl)indole

HRID 1381553Notes

Reaction equation

HRID 1381553 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH:14]([N+:16]([O-:18])=[O:17])[CH3:15])([O-])=O>CCO.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH:14]([N+:16]([O-:18])=[O:17])[CH3:15]

Participants

4

Reactant 1

HCID 143911385-Nitro-3-(2-nitropropyl)indole

Product 1

HCID 143911395-Amino-3-(2-nitropropyl)indoleYield 70%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.5 g (0.006 mole) of 5-nitro-3-(2-nitropropyl)indole in 150 ml of EtOH treated with 100 mg of PtO2 was hydrogenated (Parr) for 15 minutes. The catalyst was filtered and solvent removed in vacuo to give a yellow product which solidified on standing. Recrystallization from EtOH afforded 0.9 g (70%) of desired product: m.p. 120°-121.5°.

Workup

  1. customfor 15 minutes
  2. filtrationThe catalyst was filtered
  3. customsolvent removed in vacuo
  4. customto give a yellow product which
  5. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-6ca167f6fdfa438f9d487e6cef21ca71
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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