Methyl 4-Formylbenzoate → HCID 59846206, compound

HRID 1261753Notes

Reaction equation

HRID 1261753 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.C[O-].[Na+].[CH:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)=O>CO>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:31]=[CH:32][C:23](/[CH:21]=[CH:9]/[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 10942334Sodium MethoxideHCID 598461761-(4-Chloro-2-phenylaminophenyl)ethanone

Product 1

HCID 59846206HCID 59846206, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 L 3-necked round-bottomed flask equipped with a stirrer, a nitrogen bubbler, an addition funnel and a thermometer was charged with 1-(4-chloro-2-(phenylamino)phenyl)ethanone (79.3 g, 323 mmol) and methanol (628 g, 793 mL). The reaction was treated while stirring with a solution of sodium methoxide (25 wt % in methanol, 119 mL, 520 mmol) followed by addition of methyl 4-formylbenzoate (53.0 g, 323 mmol). The reaction mixture was allowed to stir overnight. At this time, the reaction was cooled in an ice bath. The resulting solids were collected by filtration, washed with cold methanol and dried to afford 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-benzoic acid methyl ester (115 g, 90.9%) as a red solid. This material was used without further purification.

Workup

  1. customA 2 L 3-necked round-bottomed flask equipped with a stirrer
  2. additionThe reaction was treated
  3. temperatureAt this time, the reaction was cooled in an ice bath
  4. filtrationThe resulting solids were collected by filtration
  5. washwashed with cold methanol
  6. customdried

Sources & evidence

ORD record
ord-9e7d163df5f64f08b912a91d00c15cd8
Source dataset
uspto-grants-2013_06
Patent number
US08471027B2

Reaction notes

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