1,1,4,6-Tetramethyl-5,7-dinitro-2,3-dihydro-1H-indene → 3,3,5,7-Tetramethyl-2,3-dihydro-1H-indene-4,6-diamine

HRID 704482Notes

Reaction equation

HRID 704482 reaction equation
[N+:1]([C:4]1[C:5]([CH3:19])=[C:6]2[C:10](=[C:11]([N+:14]([O-])=O)[C:12]=1[CH3:13])[C:9]([CH3:18])([CH3:17])[CH2:8][CH2:7]2)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[C:5]([CH3:19])=[C:6]2[C:10](=[C:11]([NH2:14])[C:12]=1[CH3:13])[C:9]([CH3:17])([CH3:18])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 181793411,1,4,6-Tetramethyl-5,7-dinitro-2,3-dihydro-1H-indeneHCID 178418361HCID 178418361, compound

Product 1

HCID 181793183,3,5,7-Tetramethyl-2,3-dihydro-1H-indene-4,6-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

One hundred seventy-five grams (0.662 mol) of the 5,7-dinitro-1,1,4,6-tetramethylindane thus obtained were dissolved in 500 g of methanol, and after addition of 17.5 g of 5% Pd/C (water content: 50%) to the resultant solution, the mixture was stirred at 50-60° C. for 84 hours in a hydrogen gas atmosphere. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The thus-obtained residue was distilled under reduced pressure to obtain 5,7-diamino-1,1,4,6-tetramethylindane as pale yellow crystals.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. distillationThe thus-obtained residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-cdc653b5b842445fbcb0a1db009f923a
Source dataset
uspto-grants-1991_01
Patent number
US04987261

Reaction notes

Loading…