4-Chloroaniline → Glycine, N-(4-chlorophenyl)-, ethyl ester

HRID 2061405Notes

Reaction equation

HRID 2061405 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.I[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])(=O)C.[Na+]>O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 12183Ethyl iodoacetateHCID 517045Sodium Acetate

Product 1

HCID 302644Glycine, N-(4-chlorophenyl)-, ethyl esterYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloroaniline (15.5 g, 122 mmol), ethyl iodoacetate (14.4 mL, 122 mmol) and sodium acetate (20.0 g, 244 mmol) were stirred in water (24 mL) at 90° C. for 3 hours. After cooling to room temperature the precipitate was collected by filtration, washing with water (40 mL), to yield the title compound (25.6 g, 98%) as brown prisms. 1H NMR (400 MHz, CDCl3) δ 1.29 (3H, t), 3.86 (2H, s), 4.22 (2H, q), 6.53 (2H, d), 7.14 (2H, d).

Workup

  1. filtrationwas collected by filtration
  2. washwashing with water (40 mL)

Sources & evidence

ORD record
ord-20ee1a0487774d4e90e37bd6ff1acc3b
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Reaction notes

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