HCID 117716267, compound → HCID 117716311, compound

HRID 1398264Notes

Reaction equation

HRID 1398264 reaction equation
[N+:1]([C:4]1[CH:35]=[CH:34][C:7]([O:8][CH:9]([CH3:33])[C:10]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][C:19](=[O:32])[CH:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[CH3:21])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Ni]>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH:20]([CH3:21])[C:19]([O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][C:10](=[O:11])[CH:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:35][CH:34]=2)[CH3:33])=[O:32])=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 117716267HCID 117716267, compound

Product 1

HCID 117716311HCID 117716311, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(4-Nitrophenoxy)-propionic acid 2-{2-[2-(4-nitrophenoxy)-propionyloxy]-ethoxy}-ethyl ester (300 g) was dissolved in ethyl acetate (1.5 L) in a pressure vessel. Raney Nickel catalyst (290 g) was added and the mixture was stirred under an atmosphere of hydrogen (10 Kg) for 4 hour. The catalyst was removed by filtration and the solvent was distilled off under reduced pressure to obtain pure (4-aminophenoxy)-propionic acid 2-{2-[2-(4-aminophenoxy)-propionyloxy]-ethoxy}-ethyl ester (254 g) as a light yellow syrup. The product was characterized by 1H NMR (CDCl3) δ 1.60 (d, 3H, CH3), 3.20 (bs, 2H, NH2), 3.60 (t, 2H, CH2), 4.25 (t, 2H, CH2), 4.65 (q, 1H, CH), 6.60 (d, 2H, Ar), 6.75 (d, 2H, Ar).

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-396947fd0e4844d0bdab0607cbb61bee
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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