Hydrochloric Acid → HCID 54736035, compound

HRID 1632514Notes

Reaction equation

HRID 1632514 reaction equation
C(O[C:4](=[O:28])[C:5]1[C:6](=[CH:18][C:19]([CH3:27])=[C:20]([C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[CH:21]=1)[N:7]([CH2:16][CH3:17])[C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])C.[Na].Cl>C(O)C>[CH2:13]([O:12][C:10]([C:9]1[C:8](=[O:15])[N:7]([CH2:16][CH3:17])[C:6]2[C:5]([C:4]=1[OH:28])=[CH:21][C:20]([C:22](=[O:26])[CH2:23][CH2:24][CH3:25])=[C:19]([CH3:27])[CH:18]=2)=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 53859290HCID 53859290, compound

Product 1

HCID 54736035HCID 54736035, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

19.6 g of N-ethyl-5-butyryl-4-methyl-N-(1'-oxo-2'-ethoxycarbonylethyl)-anthranilic acid ethyl ester in 60 ml of absolute ethanol are added dropwise, at room temperature, to a solution of 1.15 g of sodium in 30 ml of absolute ethanol. The yellow solution is refluxed for 3 hours. The resulting suspension is then freed of ethanol in vacuo. The residue is dissolved in ice-water and acidified with hydrochloric acid. The separated oil is extracted with methylene chloride and the methylene chloride solution is washed with water, dried over sodium sulphate, filtered and concentrated to dryness by evaporation in vacuo. An oil is obtained, which is caused to crystallise from methanol. In this manner 1-ethyl-6-butyryl-4-hydroxy-7-methylcarbostyril-3-carboxylic acid ethyl ester having a melting point of 124°-126° is obtained.

Workup

  1. temperatureThe yellow solution is refluxed for 3 hours
  2. extractionThe separated oil is extracted with methylene chloride
  3. washthe methylene chloride solution is washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness by evaporation in vacuo
  7. customAn oil is obtained
  8. customto crystallise from methanol

Sources & evidence

ORD record
ord-c004b537373d492a850cd6ca05b9c427
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

Loading…