Aniline → N-Phenylglycine ethyl ester

HRID 1494561Notes

Reaction equation

HRID 1494561 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:9]1([NH:8][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 7748Ethyl bromoacetate

Product 1

HCID 75190N-Phenylglycine ethyl esterYield 70%

Procedure

To a 250 mL round-bottom flask equipped with addition funnel and argon inlet was added 50 mL of aniline III which was stirred mechanically at 0° C. under argon atmosphere Ethyl bromoacetate, 25 mL (224 mmol) was added in dropwise fashion over 60 min. The mixture slowly solidified and was allowed to stand unstirred at -25° C. for 18 hours. The solid was chipped from the flask and partitioned between dichloromethane (CH2Cl2) and water. The aqueous layer was made basic with 20 mL 50 NaOH solution and extracted with CH2Cl2. The combined organic layers were washed well with H2O, dried over MgSO4 and concentrated. The residue was crystallized from hexane containing a trace of CH2Cl2. Total yield was 28 g (156 mmol, 70% yield) based on ethyl bromoacetate used. mp. 54°-55° C., 'H-NMR (CDCl3) ppm δ7.19 (t, 2 H, J= 7 Hz), 6.76 (t,1 H, J=7 Hz), 6.60 (d, 1 H, J=7 Hz), 4.24 (q, 2 H, J=7 Hz), 3.89 (S,2 H), 1.29 (t, 3 H, J=7 Hz; IR (KBr) 3420, 1742, 1610, 1520, 1220 cm-1.

Workup

  1. customTo a 250 mL round-bottom flask equipped with addition funnel and argon inlet
  2. additionwas added in dropwise fashion over 60 min
  3. custompartitioned between dichloromethane (CH2Cl2) and water
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layers were washed well with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was crystallized from hexane containing a trace of CH2Cl2

Sources & evidence

ORD record
ord-9e1fd3bff490446490716fcc0c0c80ae
Source dataset
uspto-grants-1991_06
Patent number
US05026861

Reaction notes

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