Diethyl (ethoxymethylene)malonate → Diethyl 2-[(3,4-dimethoxyanilino)methylidene]propanedioate

HRID 394990Notes

Reaction equation

HRID 394990 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].C(O[CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 227703,4-Dimethoxyaniline

Product 1

HCID 2267691Diethyl 2-[(3,4-dimethoxyanilino)methylidene]propanedioate

Conditions

Temperature
110 °C

Procedure

A mixture of 10 g of 3,4-dimethoxyaniline in 13.2 cm3 of diethyl ethoxymethylenemalonate was stirred for 1.5 hours at a temperature in the region of 110° C. After cooling to about 20° C., the reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C. 21.1 g of diethyl 2-[(3,4-dimethoxyphenylamino)methylene]malonate were obtained in the form of a brown solid.

Workup

  1. temperatureAfter cooling to about 20° C.
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C

Sources & evidence

ORD record
ord-16d9f3554458488ca3cbaa97bb4b31ff
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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