Sodium Carbonate → HCID 19426753, compound

HRID 741576Notes

Reaction equation

HRID 741576 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:12]1[C:13]([N+:26]([O-:28])=[O:27])=[C:14]2[C:19](=[C:20]([NH:22]C(=O)C)[CH:21]=1)[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:11])=[O:10])[CH3:2].O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:12]1[C:13]([N+:26]([O-:28])=[O:27])=[C:14]2[C:19](=[C:20]([NH2:22])[CH:21]=1)[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:10])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 19426745HCID 19426745, compound

Product 1

HCID 19426753HCID 19426753, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-[6-(2-Ethyl-benzenesulfonyl)-5-nitro-quinolin-8-yl]-acetamide (0.5 g) is stirred at reflux in 2N hydrochloric acid (50 mL) and 1,4-dioxane (50 mL) for 2 hours. The mixture is added to 2N sodium carbonate (200 mL) and extracted with ethyl acetate (3×100 mL). The extracts are washed with saturated brine (150 mL), dried over magnesium sulfate, filtered, and evaporated to leave an orange solid. This solid is crystallized from hot ethyl acetate to give the title compound as orange crystals; mp 213°-216° C.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe extracts are washed with saturated brine (150 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto leave an orange solid
  7. customThis solid is crystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-8705f4331fb74d4cb91294d941d732bf
Source dataset
uspto-grants-1996_09
Patent number
US05552411

Reaction notes

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