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

HRID 2104390Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:12][CH2:13][CH2:14]Br)(=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:13]([O:12][C:9](=[O:11])[CH2:10][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

4-Chloroaniline (2.0 g) was dissolved in acetonitrile (20 mL), and bromoethyl acetate (2.1 g) and potassium carbonate (2.2 g) were added thereto, followed by stirring at 60° C. for 2 days. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:chloroform=2:1), to thereby give the title compound (2.3 g).

Workup

filtrationThe reaction mixture was filtered through a Celite pad
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:chloroform=2:1)

Sources & evidence

ORD record: ord-7a72002352a2482e989a5cae54ba4a8c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576135B2

Reaction notes

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