Diethyl (ethoxymethylene)malonate → 2-[(2-Bromo-5-methoxyphenylamino)methylene]malonic acid diethyl ester

HRID 2187357Notes

Reaction equation

HRID 2187357 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[CH:6][C:7]=1[Br:8].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>>[CH2:19]([O:18][C:16](=[O:17])[C:15](=[CH:14][NH:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[CH:6][C:7]=1[Br:8])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:20]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7930162-Bromo-5-methoxyaniline

Product 1

HCID 103846312-[(2-Bromo-5-methoxyphenylamino)methylene]malonic acid diethyl ester

Conditions

Temperature
100 °C

Procedure

A mixture of 3-amino-4-bromoanisole (1.40 g) and diethyl ethoxymethylene-malonate (1.4 ml) was heated at 100° C. for 4 h. The reaction mixture was cooled and ethanol removed at reduced pressure to give the title compound as a waxy brown solid (2.55 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customethanol removed at reduced pressure

Sources & evidence

ORD record
ord-1e65fc4846a74cf5a2263fd3765b8665
Source dataset
uspto-grants-2002_06
Patent number
US06410529B1

Reaction notes

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