Hydrochloric Acid → HCID 12811139, compound

HRID 1155714Notes

Reaction equation

HRID 1155714 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[N:6]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:4]=1.C(=O)([O-])O.[Na+].[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>C(OCC)(=O)C.O>[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:34]([O:33][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:35])=[CH:13][CH:14]=2)[N:6]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 12811134HCID 12811134, compound

Product 1

HCID 12811139HCID 12811139, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 4-methyl-6-(4-aminophenyl)-2-pyridinecarboxylate hydrochloride (6 g), water (150 ml), sodium hydrogen carbonate (6 g) and ethyl acetate (150 ml) is added under ice-cooling with agitation benzyloxycarbonyl chloride (4.2 g), and the mixture is agitated for 45 minutes. The reaction mixture is made acidic with diluted hydrochloric acid, and the resulting crystals are collected by filtration, washed with water and dried. The organic layer is separated from the filtrate, washed with water and dried, and then the solvent is distilled off therefrom under reduced pressure. To the resulting residue is added ethyl acetate, and the precipitated crystals are collected by filtration and combined with the crystals obtained above to give ethyl 4-methyl-6-(4-benzyloxycarbonylaminophenyl)-2-pyridinecarboxylate (6 g). M.P. 184°-185° C.

Workup

  1. additionis added under ice-
  2. filtrationthe resulting crystals are collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe organic layer is separated from the filtrate
  6. washwashed with water
  7. customdried
  8. distillationthe solvent is distilled off
  9. additionTo the resulting residue is added ethyl acetate
  10. filtrationthe precipitated crystals are collected by filtration
  11. customobtained above

Sources & evidence

ORD record
ord-12e0c29ea12c49d19f8ddd921f0c03a2
Source dataset
uspto-grants-1982_06
Patent number
US04332809

Reaction notes

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