Sodium Hydroxide → HCID 59846206, compound

HRID 1697074Notes

Reaction equation

HRID 1697074 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.[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=1.[OH-].[Na+]>CO>[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24](/[CH:27]=[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:23][CH:22]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15294Methyl 4-FormylbenzoateHCID 598461761-(4-Chloro-2-phenylaminophenyl)ethanone

Product 1

HCID 59846206HCID 59846206, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(4-chloro-2-phenylaminophenyl)-ethanone (1.7 g, 6.9 mmol), 4-formyl-benzoic acid methyl ester (1.14 g, 6.9 mmol) and NaOH (2 M aq, 2 mL) in MeOH (30 mL) was stirred at RT overnight. The precipitate formed was collected by filtration and dried in a vacuum oven to afford 0.7 g of 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-benzoic acid methyl ester as an orange solid. The mother liquors were acidified by adding glacial HOAc (99%) to pH 5, and the resulting mixture extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to yield 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-benzoic acid (350 mg).

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-aee867a9b39342ddb19c8f2ec90a1f5d
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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