Hydrochloric Acid → HCID 67193464, compound

HRID 1853247Notes

Reaction equation

HRID 1853247 reaction equation
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]([O:15][CH3:16])=O)[N:4]=1.O[C:18]1[CH:23]=[CH:22][CH:21]=C[C:19]=1[C:24](=[O:26])[CH3:25].Cl>N1C=CC=CC=1>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]2[O:15][C:16]3[C:19]([C:24](=[O:26])[CH:25]=2)=[CH:18][CH:23]=[CH:22][CH:21]=3)[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 83752'-HydroxyacetophenoneHCID 24758Sodium hydrideHCID 725374Methyl 3-isoquinolinecarboxylate

Product 1

HCID 67193464HCID 67193464, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
90 °C

Procedure

To a suspension of sodium hydride (60% in mineral oil, 227 mg, 5.7 mmol) in dry pyridine (4 ml) was added dropwise a solution of methyl isoquinoline-3-carboxylate (390 mg, 2.08 mmol) and 2′-hydroxy-acetophenone (257 mg, 1.89 mmol) in dry pyridine (4 ml). The mixture was heated at 90° C. for 15 min., cooled to room temperature and poured into an ice cooled 1N hydrochloric acid aqueous solution. The product was extracted in dichloromethane. The organic layers were washed with a 1N hydrochloric acid solution, brine, dried over sodium sulfate and concentrated to dryness. The residue was dissolved in acetic acid (10 ml) and treated with sulfuric acid (40 μl). The solution was heated to 100° C. for 30 min. and cooled to room temperature. The solvents were removed under vacuum distillation. The solid was triturated in water, filtered, washed with a saturated solution of sodium hydrogenocarbonate and water. The solid was dried under vacuum to yield 2-Isoquinolin-3-yl-chromen-4-one (459 mg, 89%) as beige solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe product was extracted in dichloromethane
  3. washThe organic layers were washed with a 1N hydrochloric acid solution, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was dissolved in acetic acid (10 ml)
  7. additiontreated with sulfuric acid (40 μl)
  8. temperatureThe solution was heated to 100° C. for 30 min.
  9. temperaturecooled to room temperature
  10. customThe solvents were removed under vacuum distillation
  11. customThe solid was triturated in water
  12. filtrationfiltered
  13. washwashed with a saturated solution of sodium hydrogenocarbonate and water
  14. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-0d355ef42a1b4b09bc1f522598d9b2d8
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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