4-Chloroaniline → HCID 22769951, compound

HRID 1764067Notes

Reaction equation

HRID 1764067 reaction equation
[C:1]([C:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])O[C:6]=1[CH3:13])([O:3][CH3:4])=[O:2].[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([N:19]2[C:8]([CH3:12])=[CH:9][C:10](=[O:11])[C:5]([C:1]([O:3][CH3:4])=[O:2])=[C:6]2[CH3:13])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 122813714H-Pyran-3-carboxylic acid, 2,6-dimethyl-4-oxo-, methyl ester

Product 1

HCID 22769951HCID 22769951, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

40 g of 3-carbomethoxy-2,6-dimethylpyr-4-one and 30.2 g of 4-chloroaniline are dissolved in 400 ml of toluene along with 400 mg of p-toluenesulfonic acid monohydrate. The reaction mixture is refluxed for 4 hours. The solvent is removed and the product crystallized from ether to yield 30 g of N-(4-chlorophenyl)-3-carbomethoxy-2,6-dimethylpyrid-4-one (m.p. 189°-90°).

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customThe solvent is removed
  3. customthe product crystallized from ether

Sources & evidence

ORD record
ord-4bcf79800f6f4e94b3f0b141481c4046
Source dataset
uspto-grants-1978_09
Patent number
US04115101

Reaction notes

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