2-Naphthol → HCID 13821930, compound

HRID 1731288Notes

Reaction equation

HRID 1731288 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][N:7]=1)[C:3](Cl)=[O:4].[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[OH:23].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[CH3:1][N:2]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][N:7]=1)[C:3](=[O:4])[O:23][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 13489290HCID 13489290, compound

Product 1

HCID 13821930HCID 13821930, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1.85 g of N-methyl-N-(4-methyl-2-pyridyl)carbamoyl chloride, 1.44 g of 2-naphthol and 1.38 g of anhydrous potassium carbonate in methylethylketone was refluxed under heating for 48 hours. After the reaction mixture was cooled to room temperature, inorganic salts were removed by filtration and then methylethylketone was removed by distillation under a reduced pressure. The residue was purified by the column chromatography (silica gel, developed with ethyl acetate/benzene=1/9 (V/V) ), to obtain 2.37 g of oily 2-naphthyl N-methyl-N-(4-methyl-2-pyridyl)carbamate (yield 81%, refraction index nD25 1.6191). The elementary analysis of this material was as follows:

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 48 hours
  3. custominorganic salts were removed by filtration
  4. custommethylethylketone was removed by distillation under a reduced pressure
  5. customThe residue was purified by the column chromatography (silica gel, developed with ethyl acetate/benzene=1/9 (V/V) )

Sources & evidence

ORD record
ord-5a76f4092bb34f58bd63fdbe5fda44a5
Source dataset
uspto-grants-1986_11
Patent number
US04621090

Reaction notes

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