HCID 22153790, compound → HCID 20300404, compound

HRID 2083630Notes

Reaction equation

HRID 2083630 reaction equation
[N+:1]([C:4]1[C:12]2[N:11]=[N:10][N:9]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[C:12]2[N:11]=[N:10][N:9]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 22153790HCID 22153790, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20300404HCID 20300404, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

In a 500 ml. Paar hydrogenator is placed 49.2 g. of the 4-nitro-1-cyclohexyl-1H-benzotriazole, 220 ml. ethanol and 2.5 g. 10% palladium on carbon catalyst and the mixture is heated to 45° C. Hydrogen is introduced at about 40 psi and the temperature of the reaction is maintained at 60° C. The reaction is over after 11/2 hours and the catalyst is then removed by filtration. On evaporation of the solvent, the product is isolated in quantitative yield as an oil, which solidifies on standing, m.p. 54°-60° C. Analysis Calcd. for C12H16N4 : C, 66.64; H, 7.46; N, 25.90. Found: C, 66.38; H, 7.55; N, 25.69.

Workup

  1. custom2 hours
  2. customthe catalyst is then removed by filtration
  3. customOn evaporation of the solvent
  4. customthe product is isolated in quantitative yield as an oil, which

Sources & evidence

ORD record
ord-aa80b6ed49d14d6795451af6084009d3
Source dataset
uspto-grants-1978_04
Patent number
US04086242

Reaction notes

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