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

HRID 401223Notes

Reaction equation

HRID 401223 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10].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:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[Br:1])[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 esterYield 81.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-5-methoxy-phenylamine (540 mg, 2.64 mmol) and diethyl 2-(ethoxymethylene)malonate (600 mg, 2.7 mmol) was stirred at 100° C. for 2 h. After cooling, the reaction mixture was recrystallized from methanol (10 mL) to give 2-[(2-bromo-5-methoxy-phenylamino)-methylene]-malonic acid diethyl ester as a yellow solid (0.8 g, 81%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was recrystallized from methanol (10 mL)

Sources & evidence

ORD record
ord-ab7ac6ea9342462b8719bb9ce7fcdc6a
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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