Diethyl (ethoxymethylene)malonate → Diethyl (3,4-difluoro-2-hydroxyaniline) methylenmalonate

HRID 441118Notes

Reaction equation

HRID 441118 reaction equation
[CH2:1](O[CH:4]=[C:5]([C:11]([O:13]CC)=[O:12])[C:6]([O:8]CC)=[O:7])[CH3:2].[NH2:16][C:17]1[C:22]([OH:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][CH:18]=1.[CH3:26][CH2:27]CCCCC>>[CH2:1]([N:16]([CH2:26][CH3:27])[C:17]1[CH:18]=[CH:19][C:20]([F:25])=[C:21]([F:24])[C:22]=1[OH:23])[CH3:2].[CH2:4]=[C:5]([C:11]([O-:13])=[O:12])[C:6]([O-:8])=[O:7]

Participants

4

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 8900HeptaneHCID 27784416-Amino-2,3-difluorophenol

Product 1

HCID 86749519Diethyl (3,4-difluoro-2-hydroxyaniline) methylenmalonateYield 81%

Procedure

13.44 ml (66.34 mmol) of diethyl ethoxymethylenmalonate of are added to a solution of 9.6 g (66.34 mmol) of 3,4-difluoro-2-hydroxy-aniline [3] in 50 ml of n-heptane. The reaction mixture is reflux heated for 1 hour and then cooled at room temperature until a precipitate is obtained which is filtered at vacuum and washed with 20 ml of n-heptane. 17.5 g (81%) of diethyl (3,4-difluoro-2-hydroxyaniline)-methylenmalonate [4] are obtained and it does not need to be subject to a subsequent purification treatment.

Workup

  1. temperatureThe reaction mixture is reflux
  2. temperatureheated for 1 hour
  3. customis obtained which
  4. filtrationis filtered at vacuum
  5. washwashed with 20 ml of n-heptane

Sources & evidence

ORD record
ord-401390106cc14a8082bf3a9afc5e244d
Source dataset
uspto-grants-1996_05
Patent number
US05521310

Reaction notes

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