HCID 19835547, compound → HCID 19835523, compound

HRID 477383Notes

Reaction equation

HRID 477383 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][NH2:9].[H][H]>[Pd]>[ClH:1].[ClH:1].[ClH:1].[NH2:2][C:3]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][NH2:9]

Participants

4

Reactant 2

HCID 19835547HCID 19835547, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19835523HCID 19835523, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

0.02 mol (5.3 g) of the 1-(2'-amino-4'-nitrophenoxy)-3-aminopropan-2-ol monohydrochloride prepared according to Example 4 is introduced into 50 ml of 96° strength alcohol and 0.2 g of 10% strength palladium-on-charcoal. The mixture is heated at 85° C. for one hour under 35 bars of hydrogen. After cooling, it is filtered to remove the catalyst, the filtrate being collected in 20 ml of iced ethanol saturated with hydrogen chloride. The expected product precipitates in the form of the trihydrochloride. After recrystallisation of this trihydrochloride from an ethanol/water mixture, it melts with decomposition at 236°-238° C.

Workup

  1. temperatureAfter cooling
  2. filtrationit is filtered
  3. customto remove the catalyst
  4. customthe filtrate being collected in 20 ml of iced ethanol saturated with hydrogen chloride
  5. customThe expected product precipitates in the form of the trihydrochloride
  6. customAfter recrystallisation of this trihydrochloride from an ethanol/water mixture, it
  7. custommelts with decomposition at 236°-238° C.

Sources & evidence

ORD record
ord-f16c3c82dfc74dba91634ea2c3527506
Source dataset
uspto-grants-1989_12
Patent number
US04888025

Reaction notes

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