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

HRID 1358906Notes

Reaction equation

HRID 1358906 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.O>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 962WaterHCID 181793411,1,4,6-Tetramethyl-5,7-dinitro-2,3-dihydro-1H-indene

Product 1

HCID 181793183,3,5,7-Tetramethyl-2,3-dihydro-1H-indene-4,6-diamineYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

175 g (0.662 mol) of the resulted 5,7-dinitro-1,1,4,6-tetramethylindan was dissolved in 500 g of methanol, 17.5 g (50% water content) of 5%-Pd/C was added, then, the mixture was stirred for 84 hours at 50 to 60° C. under a hydrogen atmosphere. After completion of the reaction, the mixture was filtrated and filtrate was concentrated under reduced pressure. The resulted residue was distilled under reduced pressure to obtain 5,7-diamino-1,1,4,6-tetramethyl-indan as a pale yellow crystal. The yielded amount was 124 g (yield: 92.1%), the melting point was 77 to 78.5° C., and the boiling point was 148 to 150° C. (339 Pa).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtrated
  3. concentrationfiltrate was concentrated under reduced pressure
  4. distillationThe resulted residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-76301bff213945b490d0dd14ed2d51f0
Source dataset
uspto-grants-2003_07
Patent number
US06599675B2

Reaction notes

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