Pyridine → HCID 67508600, compound

HRID 1431336Notes

Reaction equation

HRID 1431336 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[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22]>>[Cl:19][C:20]1[CH:26]=[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 72402-ChloroanilineHCID 11857Diethyl methylmalonate

Product 1

HCID 67508600HCID 67508600, compound

Procedure

The ester was prepared according to Procedure A using diethyl 2-methylmalonate (6.1 mL, 35.3 mmol), pyridine (3.80 mL, 47.0 mmol) and 2-chloroaniline (3.00 g, 23.52 mmol). The reaction mixture was heated for 6 days. The residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes) to give ethyl 3-(2-chlorophenylamino)-2-methyl-3-oxopropanoate. Mass Spectrum (ESI) m/e=256.1 (M+1).

Workup

  1. customThe ester was prepared
  2. temperatureThe reaction mixture was heated for 6 days
  3. customThe residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-acd17f8551604a1eb7a9e0dcf9e13004
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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