HCID 13343739, compound → HCID 10262853, compound

HRID 745567Notes

Reaction equation

HRID 745567 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([N+:14]([O-])=O)[C:5]([N+:17]([O-])=O)=[CH:4][C:3]1=2>CO.[Ni]>[CH3:12][C:9]1([CH3:13])[CH2:10][CH2:11][C:2]([CH3:1])([CH3:20])[C:3]2[CH:4]=[C:5]([NH2:17])[C:6]([NH2:14])=[CH:7][C:8]1=2

Participants

4

Reactant 1

HCID 13343739HCID 13343739, compound

Product 1

HCID 10262853HCID 10262853, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

39.0 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2,3-dinitro-naphthalene in 1300 ml of methanol were hydrogenated with Raney-nickel in a 2 l hydrogenation flask. The H2 -uptake after 48 hours was 20.7 l (18.8 l=theory). The catalyst was removed by filtration under suction, the solution was again filtered and the filtrate was evaporated in vacuo. The residue was crystallized from isopropanol. There were obtained 26.2 g (85.5% of theory) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2,3-naphthalene-diamine of melting point 188°-189° C.

Workup

  1. customThe catalyst was removed by filtration under suction
  2. filtrationthe solution was again filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-04d00a405368467b828d8a5dd6b78649
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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