(4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester → HCID 59253947, compound

HRID 1882329Notes

Reaction equation

HRID 1882329 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:19])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)=[O:4]>CN(C)C=O.[Pd]>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:19])[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)=[O:4]

Participants

4

Reactant 1

HCID 59253951(4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester

Product 1

HCID 59253947HCID 59253947, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

(4-Nitro-phenoxy)-acetic acid methoxycarbonylmethyl ester 95 (20 grams, 74.3 mmol) was dissolved in dimethyl formamide (100 mL) in a pressure vessel, palladium on carbon (5%, 8 grams) added, and the mixture stirred under an atmosphere of H (4 Kg) for 2 hours. The catalyst was removed by filtration and to the filtrate; ice water (400 mL) was added. Crude 96 was extracted into ethyl acetate, dried over Na2SO4 and distilled, crude 3 was recrystallized from chloroform:hexane (1:6) to get pure 96 (13 grams, 73%) as a light brown shining powder. M.p: 76.5-78.5° C. IH NMR (CDCl3) δ 3.32 (bs, 2H, NH2), 3.76 (s, 3H, Ester), 4.70 (s, 2H, OCH2), 4.74 (s, 2H, OCH2), 6.60 (d, 2H, Ar), 6.74 (d, 2H, Ar).

Workup

  1. customThe catalyst was removed by filtration and to the filtrate
  2. additionice water (400 mL) was added
  3. extractionCrude 96 was extracted into ethyl acetate
  4. dry with materialdried over Na2SO4
  5. distillationdistilled
  6. customcrude 3 was recrystallized from chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-66e0a2a08afe4b4195e197f719961e22
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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