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

HRID 868144Notes

Reaction equation

HRID 868144 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].CCO[CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[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

4

Reactant 2

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

Product 1

HCID 2267691Diethyl 2-[(3,4-dimethoxyanilino)methylidene]propanedioateYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dimethoxyaniline (100 g, 0.65 mol) in 130 ml of N,N-dimethylformamide was added diethyl ethoxymethylene malonate (141.2 g, 0.65 mol). The mixture was stirred at room temperature for 21 hours. The solvent was evaporated in vacuo and the residual dark brown oil was recrystallized from 1.6 l cyclohexane and 50 g of activated carbon to give 150.5 g of desired product. Extraction of the carbon with hot cyclohexane gave another 27.1 g of product. Total yield 177.6 g, melting point 57°-59° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residual dark brown oil was recrystallized from 1.6 l cyclohexane and 50 g of activated carbon

Sources & evidence

ORD record
ord-8b92b02ceec3421aa0330faf7183932b
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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