HCID 117716334, compound → HCID 86294322, compound

HRID 1398252Notes

Reaction equation

HRID 1398252 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[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:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 117716334HCID 117716334, compound

Product 1

HCID 86294322HCID 86294322, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-(4-nitrophenoxy)-hexanoic acid 4-nitrophenyl ester (20 g) was dissolved in ethyl acetate (150 ml) in a pressure vessel. Palladium on carbon (50% wet, 3 grams) was added as a catalyst and the mixture was stirred under an atmosphere of hydrogen (5 Kg) for 1 hour. The catalyst was removed by filtration and the solvent was distilled off under reduced pressure, and the residue was triturated with cold hexane, filtered, and dried to give pure 6-(4-aminophenoxy)-hexanoic acid 4-amino-phenyl ester (11 grams) as off-white powder with a melting point of 99-101° C. The product was characterized by 1H NMR (CDCl3) δ 1.60 (m, 2H, CH2), 1.85 (m, 6H, CH2X2), 2.55 (t, 2H, CH2), 3.50 (bs, 4H, NH2), 3.90 (t, 2H, CH2), 6.60 to 6.90 (m, 8H, Ar).

Workup

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

Sources & evidence

ORD record
ord-4749bd9c899648ce90fa26229d1228a5
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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