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

HRID 1084909Notes

Reaction equation

HRID 1084909 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 (0.25 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-b3147b1974534f7982e678e15096363f
Source dataset
uspto-grants-1991_04
Patent number
US05006561

Reaction notes

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