Pyridine → Ethyl 3-(2-chloro-3-fluorophenylamino)-2-methyl-3-oxopropanoate

HRID 1431462Notes

Reaction equation

HRID 1431462 reaction equation
[CH3:1][CH:2]([C:8]([O:10]CC)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C=CC=CC=1.[Cl:19][C:20]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22]>>[Cl:19][C:20]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][C:8](=[O:10])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 11857Diethyl methylmalonateHCID 888842-Chloro-3-fluoroaniline

Product 1

HCID 59631446Ethyl 3-(2-chloro-3-fluorophenylamino)-2-methyl-3-oxopropanoate

Procedure

The ester was prepared according to Procedure A using diethyl 2-methylmalonate (5.32 mL, 30.9 mmol), pyridine (3.33 mL, 41.2 mmol) and 2-chloro-3-fluoroaniline (3.00 g, 20.61 mmol) over 7 days. The residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes) to give ethyl 3-(2-chloro-3-fluorophenylamino)-2-methyl-3-oxopropanoate as a red oil. Mass Spectrum (ESI) m/e=274.0 (M+1).

Workup

  1. customThe ester was prepared
  2. customThe residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a709146876ef4a22b23d87e71d3a9f7f
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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