Water → HCID 20494956, compound

HRID 1074862Notes

Reaction equation

HRID 1074862 reaction equation
[Cl:1][C:2]1[C:3](=[O:13])[C:4]([C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:8])O[CH:7]=1.[CH3:14][C:15]1[CH:21]=[C:20]([CH3:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:16]=1[NH2:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N+:23]([C:19]1[CH:18]=[C:16]([N:17]2[CH:7]=[C:2]([Cl:1])[C:3](=[O:13])[C:4]([C:9]([O:11][CH3:12])=[O:10])=[C:5]2[CH3:8])[C:15]([CH3:14])=[CH:21][C:20]=1[CH3:22])([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 2280072,4-Dimethyl-5-nitroanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 20494972HCID 20494972, compound

Product 1

HCID 20494956HCID 20494956, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10.1 g (0.05 mol) 5-chloro-3-methoxycarbonyl-2-methyl-4-pyranone, 8.5 g 2,4-dimethyl-5-nitroaniline and 0.1 g p-toluenesulfonic acid monohydrate in 100 ml of toluene are refluxed for 8 h in a water separator apparatus. The mixture is allowed to cool and the precipitating product is filtered off, washed with a small amount of ethylacetate/petrolether and dried. Yield: 15.0 g (85.5%) 1-(3'-nitro-4',6'-dimethylphenyl)-5-chloro-3-methoxycarbonyl-2-methyl-4-pyridone, mp. 266° C.

Workup

  1. temperatureto cool
  2. filtrationthe precipitating product is filtered off
  3. washwashed with a small amount of ethylacetate/petrolether
  4. customdried

Sources & evidence

ORD record
ord-f30551da79934ea09254503c21bbfa20
Source dataset
uspto-grants-1983_07
Patent number
US04394156

Reaction notes

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