8-Hydroxyquinoline → HCID 178513320, compound

HRID 2172682Notes

Reaction equation

HRID 2172682 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:12][OH:13].Cl.C([O-])([O-])=O.[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CCO.O>[OH:13][NH:12][C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[NH:2]

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 120874-Cyanobenzoic acidHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513320HCID 178513320, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To 4-cyanobenzoic acid (5 g, 34.0 mmol) in EtOH (150 mL) were added NH2OH.HCl (4.96 g, 71.4 mmol) in water (15 mL) and K2CO3 (7.51 g, 54.4 mmol) in water (30 mL) then 8-hydroxyquinoline (0.064 g, 0.442 mmol). The reaction was stirred at reflux temperature for 4 h. The solvent was removed in vacuo. Water (150 mL) was added and the pH adjusted to 3 using 2M HCl. The white precipitate was filtered off and washed with water to yield E-50734-EXPO37 (3.37 g, 18.71 mmol, 55.0% yield) as a white solid. The mother liquor was extracted with ethyl acetate (75 mL) twice. The combined organics were dried, filtered and condensed in vacuo to obtain: 571 mg (2.54 mmol, 8.0%, 80% purity) as green solid.

Workup

  1. temperatureat reflux temperature for 4 h
  2. customThe solvent was removed in vacuo
  3. additionWater (150 mL) was added
  4. filtrationThe white precipitate was filtered off
  5. washwashed with water
  6. customto yield E-50734-EXPO37 (3.37 g, 18.71 mmol, 55.0% yield) as a white solid
  7. extractionThe mother liquor was extracted with ethyl acetate (75 mL) twice
  8. customThe combined organics were dried
  9. filtrationfiltered
  10. customcondensed in vacuo
  11. customto obtain

Sources & evidence

ORD record
ord-1cd8592c1a0f4621afd4f2c478cb0f8e
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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