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

HRID 1098731Notes

Reaction equation

HRID 1098731 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-Nitrophenoxy)-acetic acid methoxycarbonyl methyl ester 44 (20 g, 74.3 mmol) was dissolved in dimethyl formamide (100 ml) in a pressure vessel. Palladium on carbon (5%, 8 g) was added, and the mixture stirred under an atmosphere of hydrogen (4 kg) for 2 hours. The catalyst was removed by filtration and ice water (400 ml) was added to the filtrate. Crude 45 was extracted into ethyl acetate, dried over Na2SO4 and distilled. Crude 45 was then recrystallised from chloroform:hexane (1:6) to get pure 45 (13 g, 73%) as a light brown shining powder with an m.p. between 76.5-78.5° C.

Workup

  1. customThe catalyst was removed by filtration and ice water (400 ml)
  2. additionwas added to the filtrate
  3. extractionCrude 45 was extracted into ethyl acetate
  4. dry with materialdried over Na2SO4
  5. distillationdistilled
  6. customCrude 45 was then recrystallised from chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-b7c1a5d252944419a70f3eb0ef944570
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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