Methanol → 2-Propenoic acid, 3-[4-(acetylamino)phenyl]-2-cyano-, methyl ester

HRID 543280Notes

Reaction equation

HRID 543280 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])#[N:14].CO>N1CCCCC1.C(Cl)Cl>[C:13]([C:15](=[CH:9][C:8]1[CH:11]=[CH:12][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1)[C:16]([O:18][CH3:19])=[O:17])#[N:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 7747Methyl cyanoacetateHCID 739424-Acetamidobenzaldehyde

Product 1

HCID 3341472-Propenoic acid, 3-[4-(acetylamino)phenyl]-2-cyano-, methyl ester

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of p-acetamidobenzaldehyde (4.08 g, 0.025 m), methyl cyanoacetate (2.50 g, 0.026 m), methanol (75 ml) and piperidine (10 drops) is heated and stirred at reflux for 0.5 hour. The reaction mixture is cooled and the pale yellow solid collected by filtration and dried in air. Recrystallization of the product from 50/50 isopropanol/toluene (by volume) gives 4.5 g of pure UV absorber product by mass spectrum analysis which has an absorption maximum at 346 nm in methylene chloride.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 0.5 hour
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe pale yellow solid collected by filtration
  5. customdried in air
  6. customRecrystallization of the product from 50/50 isopropanol/toluene (by volume)
  7. customgives 4.5 g of pure UV absorber product by mass spectrum analysis which

Sources & evidence

ORD record
ord-047776c6b3e340ba8177d43657fb9583
Source dataset
uspto-grants-1987_04
Patent number
US04661566

Reaction notes

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