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

HRID 2405196Notes

Reaction equation

HRID 2405196 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-fcd9618328d74331bc156efe23fe9553
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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