Sulfuric Acid → HCID 19026184, compound

HRID 1195167Notes

Reaction equation

HRID 1195167 reaction equation
S(=O)(=O)(O)O.O[C:7]1([CH3:25])[CH2:16][CH2:15][CH2:14][C:13]2[N:12]=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=[CH:9][C:8]1=2.[OH-:26].[Na+].[C:28](#[N:30])[CH3:29]>>[CH3:25][C:7]1([NH:30][C:28](=[O:26])[CH3:29])[CH2:16][CH2:15][CH2:14][C:13]2[N:12]=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=[CH:9][C:8]1=2

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 10061627HCID 10061627, compound

Product 1

HCID 19026184HCID 19026184, compoundYield 16%

Procedure

Conc sulfuric acid (70 ml) was added dropwise over 45 mins to a solution of 5,6,7,8-tetrahydro-5-hydroxy-5-methyl-2-(phenylmethoxy)quinoline (14.0 g) and acetonitrile (200 ml) at 0° C. The solution was stirred at room temperature for 18 hrs, poured over ice, and basified to pH 8 with 50% sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was purified by colmn chromatography (silica gel, elution with ethyl acetate). The appropriate fractions were collected and evaporated. Recrystallization (twice) of the residue from ethyl acetate/hexanes gave 2.60 g (16%) of product, mp 153°-154° C.

Workup

  1. additionpoured over ice
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by colmn chromatography (silica gel, elution with ethyl acetate)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customRecrystallization (twice) of the residue from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1af7e26c28df484da406ebb042c50891
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

Loading…