HCID 12223910, compound → HCID 22184611, compound

HRID 1199999Notes

Reaction equation

HRID 1199999 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O>C(O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]

Participants

4

Reactant 1

HCID 12223910HCID 12223910, compound

Product 1

HCID 22184611HCID 22184611, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Hydroxybutylamino)nitrobenzene (30 g) was dissolved in ethanol (200 ml) containing 10% palladium-on-carbon (1 g) and hydrogentated at room temperature for 3 hours under pressure (50 p.s.i.=344.7 kPa). The solution was filtered and evaporated under vacuum and the residue chromatographed on silica eluting with ethyl acetate. The fractions containing the product were evaporated under vacuum to give the title compound, (23.2 g), which was used directly in the next step.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated under vacuum
  3. customthe residue chromatographed on silica eluting with ethyl acetate
  4. additionThe fractions containing the product
  5. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-f69b1884433e47209587682e16967965
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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