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

HRID 2405187Notes

Reaction equation

HRID 2405187 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-e7d5cbf9b5d842bbbe10bb35fbca55ea
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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