2-(3-Ethoxyphenoxy)-N-(4-hydroxy-2-nitrophenyl)acetamide → N-(2-Amino-4-hydroxyphenyl)-2-(3-ethoxyphenoxy)acetamide

HRID 537312Notes

Reaction equation

HRID 537312 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[N+:19]([O-])=O)=[O:10])[CH3:2]>[Pd].C1COCC1>[NH2:19][C:13]1[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]=1[NH:11][C:9](=[O:10])[CH2:8][O:7][C:6]1[CH:22]=[CH:23][CH:24]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1

Participants

4

Reactant 1

HCID 866892912-(3-Ethoxyphenoxy)-N-(4-hydroxy-2-nitrophenyl)acetamide

Product 1

HCID 86689290N-(2-Amino-4-hydroxyphenyl)-2-(3-ethoxyphenoxy)acetamideYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 2 L hydrogenation vessel was charged with phenol 63b (12.1 g, 36.4 mmol) and THF (240 mL). To the resultant solution was added 10% Pd/C (1.2 g), and the mixture was hydrogenated at 49 psi for 2 hr. The catalyst was filtered off on glass fiber paper, and concentrated to a red oil. The crude oil crystallized with CH2Cl2 and was triturated with CH2Cl2:hexanes 1:1 (100 mL). The crystals were filtered, pressed with rubber dam, and rinsed with CH2Cl2:hexanes 1:1 (2×20 mL). The crystals were dried to give 10.1 g of 64 as yellow crystals (92%). HPLC analysis (10:10:80 H2O:A1:MeOH) showed a purity of greater than 99% with a retention time of 3.1 min.

Workup

  1. filtrationThe catalyst was filtered off on glass fiber paper
  2. concentrationconcentrated to a red oil
  3. customThe crude oil crystallized with CH2Cl2
  4. customwas triturated with CH2Cl2:hexanes 1:1 (100 mL)
  5. filtrationThe crystals were filtered
  6. washrinsed with CH2Cl2:hexanes 1:1 (2×20 mL)
  7. customThe crystals were dried

Sources & evidence

ORD record
ord-312a4716cf7944f8a472c3a97c784470
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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