2-Nitro-3-{2-(2,4-di-t-amylphenoxy)butanamido}-4-chloro-6-benzamidophenol → 2-Amino-3-{2-(2,4-di-t-amylphenoxy)butanamido}-4-chloro-6-benzamidophenol

HRID 1904889Notes

Reaction equation

HRID 1904889 reaction equation
[N+:1]([C:4]1[C:9]([NH:10][C:11](=[O:32])[CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH2:25][CH3:26])([CH3:24])[CH3:23])=[CH:18][C:17]=2[C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH2:13][CH3:14])=[C:8]([Cl:33])[CH:7]=[C:6]([NH:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:5]=1[OH:43])([O-])=O>O1CCCC1.C(O)C.[Pd]>[NH2:1][C:4]1[C:9]([NH:10][C:11](=[O:32])[CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH2:25][CH3:26])([CH3:23])[CH3:24])=[CH:18][C:17]=2[C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH2:13][CH3:14])=[C:8]([Cl:33])[CH:7]=[C:6]([NH:34][C:35](=[O:42])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:5]=1[OH:43]

Participants

5

Reactant 1

HCID 200362042-Nitro-3-{2-(2,4-di-t-amylphenoxy)butanamido}-4-chloro-6-benzamidophenol

Product 1

HCID 200362022-Amino-3-{2-(2,4-di-t-amylphenoxy)butanamido}-4-chloro-6-benzamidophenol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of tetrahydrofuran and 100 ml of ethanol was dissolved 21 g (13×10-3 mole) of 2-nitro-3-{2-(2,4-di-t-amylphenoxy)butanamido}-4-chloro-6-benzamidophenol and hydrogenation was effected by using 1.2 g of Pd-C as a catalyst. The color of the nitro derivative disappeared in 4 hours, and the Pd-C was removed by filtration and a solvent was evaporated therefrom under reduced pressure, 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. Yield: 20 g.

Workup

  1. customthe Pd-C was removed by filtration
  2. customa solvent was evaporated
  3. extractionunder reduced pressure, followed 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

Sources & evidence

ORD record
ord-dd4333fae6384d24b38f088df7df0e08
Source dataset
uspto-grants-1989_06
Patent number
US04840883

Reaction notes

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