2-[N-Methyl-N-(4-nitrobenzyl)amino]-5-nitroindane → 5-Amino-2-[N-(4-aminobenzyl)-N-methylamino]indane

HRID 1761872Notes

Reaction equation

HRID 1761872 reaction equation
[CH3:1][N:2]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([N+:22]([O-])=O)[CH:19]=2)[CH2:14]1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=1>C(OCC)(=O)C.[Pd]>[NH2:22][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH:13]([N:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[CH:8][CH:9]=1)[CH3:1])[CH2:21]2

Participants

4

Reactant 1

HCID 148352462-[N-Methyl-N-(4-nitrobenzyl)amino]-5-nitroindane

Product 1

HCID 150232235-Amino-2-[N-(4-aminobenzyl)-N-methylamino]indaneYield 58.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-[N-Methyl-N-(4-nitrobenzyl)amino]-5-nitroindane (2.3 g) in ethyl acetate (60 ml) containing 5% Pd/C (. . . g) was stirred under a hydrogen atmosphere [206.8 kPa (30 psi)] for 1 hour at room temperature. The catalyst was then removed by filtration and the filtrate was evaporated to dryness in vacuo. The residue was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated to give the title compound (1.1 g) as an oil which was used directly without further purification.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe filtrate was evaporated to dryness in vacuo
  3. customThe residue was purified by column chromatography on silica eluting with methylene chloride
  4. additioncontaining methanol (0% up to 1%)
  5. customevaporated

Sources & evidence

ORD record
ord-834771596afe4621bc1d724c54fed46e
Source dataset
uspto-grants-1989_05
Patent number
US04829071

Reaction notes

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