Aniline → 2-(Phenylcarbamoyl)acetic acid

HRID 2193641Notes

Reaction equation

HRID 2193641 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Cl)(C)C.CC1(C)[O:19][C:18](=O)[CH2:17][C:16](=[O:21])[O:15]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:19]=[C:18]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][C:16]([OH:21])=[O:15]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6397ChlorotrimethylsilaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516892Sodium Bicarbonate

Product 1

HCID 2565932-(Phenylcarbamoyl)acetic acidYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of aniline (13 mL, 143 mmol) in DCM (290 mL) was added TMSCl (18.2 mL, 143 mmol) at room temperature and the reaction mixture was stirred for 1 hour. [Rigo, B.; Fasseur, D.; Cauliez, P. and Couturier, D. Tetrahedron Lett.; 30; 23; 1989; 3073-3076.]. 2,2-Dimethyl-1,3-dioxane-4,6-dione (20.6 g, 143 mmol) was added and combined reaction mixture was stirred overnight at room temperature, poured into saturated NaHCO3 solution and extracted with EtOAc. The aqueous phase was collected, acidified with cone. HCl to pH˜3 by addition of 2N HCl and extracted with DCM. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure affording 3-oxo-3-(phenylamino)propanoic acid (1, 16.82 g, 65% yield) as a white solid. MS (m/z): 180.0 (25%) (M+H), 202.0 (100%) (M+Na).

Workup

  1. customreaction mixture
  2. stirringwas stirred overnight at room temperature
  3. extractionextracted with EtOAc
  4. customThe aqueous phase was collected
  5. additionHCl to pH˜3 by addition of 2N HCl
  6. extractionextracted with DCM
  7. dry with materialThe organic phase was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e573857bc8f45879851ba035807fc77
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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