Ethanol → Glycine, N-(m-nitrophenyl)-, ethyl ester

HRID 1280619Notes

Reaction equation

HRID 1280619 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:15](O)[CH3:16]>O>[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 25089Glycine, N-(m-nitrophenyl)-

Product 1

HCID 19172Glycine, N-(m-nitrophenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g of 3-nitrophenylglycine are heated for 20 hours with stirring at a temperature in the region of 100° C. in 100 cm3 of absolute ethanol containing 20 cm3 of 6.5N hydrochloric ethanol. The suspension is filtered at a temperature in the region of 50° C.; the filtrate is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained is taken up in water and then extracted with about 100 cm3 of ethyl acetate. The aqueous phase is made alkaline by addition of sodium carbonate until a pH in the region of 10 is obtained. The medium is extracted with ethyl acetate; the combined extracts are washed with aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure (5 kPa) at 40° C. 1 g of ethyl 3-nitrophenylglycinate is obtained in the form of a yellow oil. (Rf=0.38 in a 95/5 by volume mixture of dichloromethane/methanol, on a Merck 60F254R silica plate)

Workup

  1. filtrationThe suspension is filtered at a temperature in the region of 50° C.
  2. concentrationthe filtrate is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  3. customThe residue obtained
  4. extractionextracted with about 100 cm3 of ethyl acetate
  5. additionby addition of sodium carbonate until a pH in the region of 10
  6. customis obtained
  7. extractionThe medium is extracted with ethyl acetate
  8. washthe combined extracts are washed with aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure (5 kPa) at 40° C

Sources & evidence

ORD record
ord-4b34fa8e198c454eb9577387cc313180
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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