Diethyl methylmalonate → HCID 59631204, compound

HRID 1431352Notes

Reaction equation

HRID 1431352 reaction equation
[CH3:1][CH:2]([C:8]([O:10]CC)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][C:15]=1[O:21][CH3:22]>N1C=CC=CC=1>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:8](=[O:10])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:16][C:15]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 11857Diethyl methylmalonateHCID 131036924-Chloro-3-methoxyaniline

Product 1

HCID 59631204HCID 59631204, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared according to Procedure A using diethyl 2-methylmalonate (4.91 mL, 28.6 mmol), pyridine (3.1 mL) and 4-chloro-3-methoxyaniline (3.00 g, 19.04 mmol). The reaction mixture was heated for 5 days. The residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes) to give ethyl 3-(4-chloro-3-methoxyphenylamino)-2-methyl-3-oxopropanoate. Mass Spectrum (ESI) m/e=286.1 (M+1).

Workup

  1. customPrepared
  2. temperatureThe reaction mixture was heated for 5 days
  3. customThe residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a52d6ccbf9e149fea8e256fedc8d037d
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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