Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate → HCID 59253936, compound

HRID 501858Notes

Reaction equation

HRID 501858 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 59253929Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate

Product 1

HCID 59253936HCID 59253936, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

[2-(4-Nitrophenoxy)ethoxy]acetic acid methyl ester 42 (1 g, 3.9 mmol) was dissolved in anhydrous ethyl acetate (20 ml). Palladium on carbon (10%, 0.1 g) was added and the mixture stirred under a hydrogen atmosphere using a balloon for 30 mins. The catalyst was filtered, the filtrate concentrated, hexane (3 ml) added, and the solid filtered to give 43(625 mg, 70.9%) as a light brown powder with a m.p. between 51-52.5° C.

Workup

  1. customfor 30 mins
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated
  4. additionhexane (3 ml) added
  5. filtrationthe solid filtered

Sources & evidence

ORD record
ord-43349388ccbf4b809296bd1db11c197f
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

Loading…