HCID 117716329, compound → HCID 86294320, compound

HRID 1398257Notes

Reaction equation

HRID 1398257 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:24])[CH:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH3:13])=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:24])[CH:12]([O:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH3:13])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 117716329HCID 117716329, compound

Product 1

HCID 86294320HCID 86294320, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-nitrophenoxy)-propionic acid 4-nitrophenyl ester (30 grams, 90.28 mmoles) was dissolved in ethyl acetate (600 ml) in a pressure vessel, palladium on carbon (50% wet, 6 grams) was added and the mixture stirred under an atmosphere of Hydrogen (5 Kg) for 30 minutes. The catalyst was removed by filtration and the solvent distilled off under reduced pressure. The residue was triturated in cold diisopropyl ether, filtered and dried to give pure 2-(4-aminophenoxy)-propionic acid 4-amino-phenyl ester (15 grams) as off-white powder. The product has a melting point of 109-111° C. The product was characterized by 1H NMR (CDCl3) δ 1.75 (d, 3H, CH3), 3.50 (bs, 2H, NH2), 4.90 (q, 1H, CH), 6.65 (m, 4H, Ar), 6.80 (m, 4H, Ar).

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent distilled off under reduced pressure
  3. customThe residue was triturated in cold diisopropyl ether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-5de3986cd0454a2cac74f623d41db447
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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