P-Anisidine → 2-(4-Methoxy-anilinomethylene)-propanedioic acid dimethyl ester

HRID 1108670Notes

Reaction equation

HRID 1108670 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CO[CH:12]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[C:14]([O:16][CH3:17])=[O:15]>C(O)C>[CH3:17][O:16][C:14](=[O:15])[C:13](=[CH:12][NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 90770Dimethyl methoxymethylenemalonate

Product 1

HCID 166812202-(4-Methoxy-anilinomethylene)-propanedioic acid dimethyl esterYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 12.3 g (0.1 Mol) of p-Anisidine in 50 ml of ethanol, a solution of 17.4 g (0.1 Mol) of Dimethyl methoxymethylenemalonate in 70 ml of ethanol was added dropwise with stirring at room temperature. After an additional hour of stirring at that temperature, the reaction mixture was cooled with an ice bath and the product cristallised spontanously. The crude solid material was isolated by filtration and washed with ethanol and gave 12.9 g of the title product which is a white solid melting at 89-91° C., UV 328 nm (E=899).

Workup

  1. stirringAfter an additional hour of stirring at that temperature
  2. temperaturethe reaction mixture was cooled with an ice bath
  3. customThe crude solid material was isolated by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-3aa558fba8b3449cb30e9da914d48a0c
Source dataset
uspto-grants-2000_05
Patent number
US06069170

Reaction notes

Loading…