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

HRID 1882320Notes

Reaction equation

HRID 1882320 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.[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 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

[2-(4-Nitrophenoxy)-ethoxy]acetic acid methyl ester 74 (1 grams, 3.9 mmol) was dissolved in anhydrous ethyl acetate (20 mL), palladium carbon (10%, 0.1 gram) added and the mixture stirred under an atmosphere of H using balloon for 30 minutes. The catalyst was filtered, the filtrate concentrate hexane (3 mL) added, filtered solid to give 75 (625 mg, 70.9%) as a light brown powder. The melting point was found to be 51-52.5° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) 3.04 (bs, 2H, NH2), 3.72 (s, 3H, ester), 3.88 (t, 2H, OCH2), 4.08 (t, 2H, OCH2), 4.20 (s, 2H, OCH2), 6.58 (d, 2H, Ar), 6.70 (d, 2H, Ar).

Workup

  1. customfor 30 minutes
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrate hexane (3 mL)
  4. additionadded
  5. filtrationfiltered solid

Sources & evidence

ORD record
ord-2acca6be9521485bbd69f060c81abbb2
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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