Hydrochloric Acid → HCID 59389272, compound

HRID 2357894Notes

Reaction equation

HRID 2357894 reaction equation
[C:1]([C:4]1[C:5]2[N:6]([N:10]=[C:11]([CH:23]3[CH2:25][CH2:24]3)[C:12]=2C(OCC2C=CC=CC=2)=O)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[K+].Cl>C(O)C.O>[C:1]([C:4]1[C:5]2[N:6]([N:10]=[C:11]([CH:23]3[CH2:25][CH2:24]3)[CH:12]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59389310HCID 59389310, compound

Product 1

HCID 59389272HCID 59389272, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The compound of Example 40 (5.57 g) was dissolved in ethanol (30 mL) and water (30 mL). To this solution, potassium hydroxide (3.70 g) was added and the mixture was stirred for 3.5 hours under reflux. Subsequently, the mixture was neutralized with concentrated hydrochloric acid and extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the resulting solid product was dissolved in toluene (150 mL). This solution was stirred for 6 hours under reflux. Subsequent removal of the solvent and purification by silica gel column chromatography (hexane:ethyl acetate=4:1 then 1:1) afforded the title compound as a yellow powder (2.64 g) (Process D).

Workup

  1. temperatureunder reflux
  2. extractionextracted three times with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe resulting solid product was dissolved in toluene (150 mL)
  7. stirringThis solution was stirred for 6 hours
  8. temperatureunder reflux
  9. customSubsequent removal of the solvent and purification by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-ac9001007ed9447aa17e7bd4bd82c129
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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