Sodium Chloride → HCID 13366704, compound

HRID 482996Notes

Reaction equation

HRID 482996 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[CH2:5][CH:6]([CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])[NH:7]2.CS(O)(=O)=O.C(OCC)(=O)C.[Cl-].[Na+]>O>[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[CH2:5][CH:6]1[CH2:13][CH2:14][CH2:15][C:16](=[O:17])[N:7]12

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 15078145HCID 15078145, compound

Product 1

HCID 13366704HCID 13366704, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 26 g. (0.098 mole) 4-[2,3-dihydro-5,7-dihydroxy-(1H)-quinolin-4-one-2-yl]butyric acid and 260 ml. methanesulfonic acid was heated under a nitrogen atmosphere at 140° C. for two hours. The reaction mixture was cooled to room temperature and poured onto 1000 ml. ice. To this was added 4 liters ethyl acetate, 1 liter water, 250 g. sodium chloride and the resulting mixture stirred at room temperature overnight. The layers were separated, the aqueous phase extracted with 4×500 ml. ethyl acetate and the combined organic layers washed with saturated sodium bicarbonate solution until the pH was 7 and no effervescence was observed. The extract was then washed with water (1000 ml.), brine (1000 ml.) and dried (MgSO4). The solvent was evaporated in vacuo, the residue redissolved in a small amount of hot ethyl acetate, diluted with ethyl ether and cooled to 0° C. The precipitated solid was collected by filtration and dried in vacuo to afford 9.4 g. (38.8%) of the title compound, M.P. 259°-268° C. (decomp.). 1H-NMR [(CD3)2SO] ppm (delta): 1.75-3.25 (m, 11H), 6.1 and 6.95 (2H, split doublets, meta aryl). Mass spectrum (m/e): 247 M+.

Workup

  1. additionA mixture of 26 g
  2. additionpoured onto 1000 ml
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with 4×500 ml
  5. washethyl acetate and the combined organic layers washed with saturated sodium bicarbonate solution until the pH was 7
  6. washThe extract was then washed with water (1000 ml.), brine (1000 ml.)
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated in vacuo
  9. dissolutionthe residue redissolved in a small amount of hot ethyl acetate
  10. additiondiluted with ethyl ether
  11. temperaturecooled to 0° C
  12. filtrationThe precipitated solid was collected by filtration
  13. customdried in vacuo
  14. customto afford 9.4 g

Sources & evidence

ORD record
ord-3199a6583e3c48e7bcfda9651fbca111
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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