Methyl chloroacetate → Methyl 2-[(3-fluorophenyl)amino]acetate

Reaction equation

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

Participants

Reactant 3

HCID 7295Methyl chloroacetate

HCID 97423-Fluoroaniline

HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 18793954Methyl 2-[(3-fluorophenyl)amino]acetate

Procedure

3-Fluoroaniline (55.5 g), methyl chloroacetate (44 ml), and sodium acetate trihydrate (114 g) were treated according to the method of Intermediate 1 to give a solid (50 g), a small sample of which (ca. 1 g) was purified by FCC eluting with System B (1:3) to give a solid which was recrystallised from petroleum ether (60°-80°) to give the title compound, m.p. 68°-69°.

Sources & evidence

ORD record: ord-3e3ab8f817d44f99a7f083b61e5e4617
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05023255

Reaction notes

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