2-{2-(2,4-Di-t-amylphenoxy)butanamido}-4-chloro-5-nitrophenol → 2-{2-(2,4-Di-t-amylphenoxy)butanamido}-4-chloro-5-aminophenol

HRID 1904891Notes

Reaction equation

HRID 1904891 reaction equation
[C:1]([C:6]1[CH:29]=[C:28]([C:30]([CH2:33][CH3:34])([CH3:32])[CH3:31])[CH:27]=[CH:26][C:7]=1[O:8][CH:9]([CH2:24][CH3:25])[C:10]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([N+:20]([O-])=O)=[CH:15][C:14]=1[OH:23])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:6]1[CH:29]=[C:28]([C:30]([CH2:33][CH3:34])([CH3:31])[CH3:32])[CH:27]=[CH:26][C:7]=1[O:8][CH:9]([CH2:24][CH3:25])[C:10]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([NH2:20])=[CH:15][C:14]=1[OH:23])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 200361932-{2-(2,4-Di-t-amylphenoxy)butanamido}-4-chloro-5-nitrophenol

Product 1

HCID 200361922-{2-(2,4-Di-t-amylphenoxy)butanamido}-4-chloro-5-aminophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 100 ml of ethanol was dissolved 30 g (61×10-3 mole) of 2-{2-(2,4-di-t-amylphenoxy)butanamido}-4-chloro-5-nitrophenol and hydrogenation was effected by using 1.5 g of Pd-C as a catalyst. The color of the nitro derivative disappeared in 2 hours, and the Pd-C was removed by filtration and ethanol was evaporated from the filtrate, followed by extraction of the residue with ethyl acetate. The ethyl acetate layer was washed with an aqueous sodium hydrogen carbonate solution and then with water, and after drying over magnesium sulfate, ethyl acetate was evaporated. 28 g of the crude product was used as such for the following reaction.

Workup

  1. customthe Pd-C was removed by filtration and ethanol
  2. customwas evaporated from the filtrate
  3. extractionfollowed by extraction of the residue with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous sodium hydrogen carbonate solution
  5. dry with materialwith water, and after drying over magnesium sulfate, ethyl acetate
  6. customwas evaporated
  7. customsuch for the following reaction

Sources & evidence

ORD record
ord-afd5f5580a3f40f69947b211027c4b3a
Source dataset
uspto-grants-1989_06
Patent number
US04840883

Reaction notes

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