HCID 117716281, compound → HCID 117716287, compound

HRID 1398260Notes

Reaction equation

HRID 1398260 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][C:19](=[O:31])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[O:11])=[CH:6][CH:5]=1)([O-])=O>CN(C)C=O.[Ni]>[NH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][C:19]([O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][C:10](=[O:11])[CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:33][CH:32]=2)=[O:31])=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 117716281HCID 117716281, compound

Product 1

HCID 117716287HCID 117716287, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

(4-nitrophenoxy)-acetic acid 2-{2-[2-(4-nitrophenoxy)-acetoxy]-ethoxy}-ethyl ester (600 g) was dissolved in dimethylformamide (1.8 l) in a pressure vessel. Raney Nickel (800 grams) added and the mixture was stirred under an atmosphere of hydrogen (20 Kg) for 3 hours. The catalyst was removed by filtration and the solution was added to cold water to precipitate the crude product. The product was filtered off, slurried in methanol and re-filtered. The compound was dried to give pure (4-aminophenoxy)-acetic acid 2-{2-[2-(4-aminophenoxy)-acetoxy]-ethoxy}-ethyl ester (428 grams) as off-white powder with a melting point of 95-97° C. The product was characterized by 1H NMR (CDCl3) δ 3.10 (bs, 2H, NH2), 3.70 (t, 2H, CH2), 4.35 (t, 2H, CH2), 4.55 (s, 2H, CH2), 6.60 (d, 2H, Ar), 6.75 (d, 2H, Ar).

Workup

  1. customThe catalyst was removed by filtration
  2. additionthe solution was added to cold water
  3. customto precipitate the crude product
  4. filtrationThe product was filtered off
  5. filtrationre-filtered
  6. customThe compound was dried

Sources & evidence

ORD record
ord-0e8531c8ff6e41b584ac5e8aa8a42215
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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