Diethyl (ethoxymethylene)malonate → HCID 59410111, compound

HRID 2404842Notes

Reaction equation

HRID 2404842 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 64220652-Bromo-5-methylaniline

Product 1

HCID 59410111HCID 59410111, compoundYield 84.1%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-5-methyl-aniline (1.0 g, 5.34 mmol) and diethyl 2-(ethoxymethylene)propanedioate (1.23 g, 5.90 mmol) was heated at 100° C. for 4 h. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was then purified via silica gel column chromatography using 1 to 60% EtOAc in hexanes to yield diethyl 2-[[(2-bromo-5-methyl-phenyl)amino]methylene]propanedioate (1.6 g, 84%). 1H NMR (300 MHz, CDCl3) δ 11.19 (d, J=13.2 Hz, 1H), 8.48 (d, J=13.2 Hz, 1H), 7.43 (d, J=8.1 Hz, 1H), 7.08 (s, 1H), 6.81 (d, J=8.1 Hz, 1H), 4.37-4.23 (m, 4H), 2.35 (s, 3H), 1.42-1.25 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-2b8c6de5b0bd455baeae3c9f38fa8c7e
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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