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

HRID 1003986

Reaction equation

HRID 1003986 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-74f41da586314de9afc8b109a0516cec
Source dataset
uspto-grants-2000_04
Patent number
US06048823

Linked notes

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