Glycine → Glycine, N-(4-nitrophenyl)-

HRID 1910767Notes

Reaction equation

HRID 1910767 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].F[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1)([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 750GlycineHCID 9590p-FluoronitrobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 12095Glycine, N-(4-nitrophenyl)-Yield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Glycine (5.31 g, 70.8 mmol) was added to a mixture of 1-fluoro-4-nitro-benzene (5.0 g, 35.4 mmol) and sodium bicarbonate (5.94 g, 70.8 mmol) in dioxane (10 mL) and water (60 mL) and heated at reflux for 6 h. The reaction mixture was cooled to room temperature and washed with ethyl acetate. The aqueous layer was acidified with 1N hydrochloric acid to pH ˜3 and extracted with ethyl acetate. The extract was washed with water, brine, dried over anhydrous sodium sulfate and concentrated to dryness to afford (4-nitro-phenylamino)-acetic acid (5.0 g, 72%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 h
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8b8eb3a99a7d4c0fbbf264e0ef371745
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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