Acetone → 3-(2,4-dichlorophenyl)-6-methyl-2(1H)-pyridone

HRID 992862

Reaction equation

HRID 992862 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH:12]O)[C:10]#[N:11].[CH3:14][C:15]([CH3:17])=O.[OH-:18].[K+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:18])[NH:11][C:15]([CH3:17])=[CH:14][CH:12]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 14830692-(2,4-Dichlorophenyl)-3-hydroxyprop-2-enenitrile

Product 1

HCID 184083253-(2,4-dichlorophenyl)-6-methyl-2(1H)-pyridoneYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

α-(2, 4-dichlorophenyl)-α-hydroxymethylene acetonitrile and 8.8 g of acetone were thoroughly mixed with 110 g of polyphosphoric acid, and the mixture was heated to about 130° C. At this temperature, an exothermic reaction started. The temperature was maintained from 130 to 140° C. for 30 minutes, while heating as the case required. The cooled mixture was poured into ice water, and this suspension was stirred for 18 hours. This crude product was stirred with ethyl acetate and an excess amount of a dilute aqueous potassium hydroxide solution to make it alkaline. The formed precipitate was collected by filtration and washed sequentially with water, ethyl acetate and diethyl ether to obtain 8.0 g (yield: 45%) of the desired product. Melting point: 266-268° C.

Workup

  1. customAt this temperature, an exothermic reaction
  2. temperatureThe temperature was maintained from 130 to 140° C. for 30 minutes
  3. temperaturewhile heating as the case
  4. filtrationThe formed precipitate was collected by filtration
  5. washwashed sequentially with water, ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-43671e8cad884076b1a4d57b37f8c04c
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Linked notes

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