Diethyl (ethoxymethylene)malonate → HCID 59410120, compound

HRID 1805101Notes

Reaction equation

HRID 1805101 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 5811103-Fluoro-4-methoxyaniline

Product 1

HCID 59410120HCID 59410120, compoundYield 78%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-fluoro-4-methoxy-aniline (0.7 g, 4.96 mmol) and diethyl 2-(ethoxymethylene)propanedioate (1.1 g, 4.96 mmol) was heated at 100° C. for 4 h. The mixture was cooled to room temperature and concentrated under reduced pressure, and then purified via silica gel column chromatography using 1 to 60% EtOAc in hexanes to yield diethyl 2-((3-fluoro-4-methoxyphenylamino)methylene)malonate (1.2 g, 78%). LC/MS: m/z 312.3 (M+H)+ at 1.69 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. custompurified via silica gel column chromatography

Sources & evidence

ORD record
ord-ef1f2b3915d84af694e4d3e022d02045
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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