Sulfuric Acid → HCID 19026184, compound

HRID 1586990Notes

Reaction equation

HRID 1586990 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 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 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-c3e8e7192f7e4ba6a20d4ddf57e95845
Source dataset
uspto-grants-1993_06
Patent number
US05216164

Reaction notes

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