HCID 13343740, compound → HCID 13343756, compound

HRID 1583772Notes

Reaction equation

HRID 1583772 reaction equation
[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][C:7]([N+:14]([O-])=O)=[C:8]([N+:11]([O-])=O)[CH:9]=2)[C:4]([CH3:18])([CH3:17])[C:3]1=[O:19]>CO.[Ni]>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[NH2:14])[C:4]([CH3:17])([CH3:18])[C:3](=[O:19])[C:2]2([CH3:20])[CH3:1]

Participants

4

Reactant 1

HCID 13343740HCID 13343740, compound

Product 1

HCID 13343756HCID 13343756, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 935NickelSolvent

Procedure

12.7 g of 1,1,3,3-tetramethyl-5,6-dinitro-2-indanone were dissolved in 500 ml of methanol in a hydrogenation flask and hydrogenated with Raney-nickel. After the H2 -uptake of 6.2 l (theory=6.15 l), the catalyst was removed by filtration under suction, the filtrate was again filtered and then evaporated in vacuo. The residue was crystallized from acetonitrile. There were obtained 9.5 g (95.5% of theory) of 5,6-diamino-1,1,3,3-tetramethyl-2-indanone of melting point 179°-180° C.

Workup

  1. customAfter the H2 -uptake of 6.2 l (theory=6.15 l), the catalyst was removed by filtration under suction
  2. filtrationthe filtrate was again filtered
  3. customevaporated in vacuo
  4. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-88855da95d7547049e1299fbe999c133
Source dataset
uspto-grants-1985_11
Patent number
US04554280

Reaction notes

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