Hydrochloric Acid → HCID 117737506, compound

HRID 1750881Notes

Reaction equation

HRID 1750881 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[C:15]([N+:21]([O-])=O)[C:16]([CH3:20])=[CH:17][CH:18]=3)[CH:13]=[CH:12][N:11]=2)=[CH:5][C:4]=1[CH2:24][N:25]([CH3:27])[CH3:26]>[Fe].C(O)C.O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[CH:18]=[CH:17][C:16]([CH3:20])=[C:15]([NH2:21])[C:14]=3[CH:13]=[CH:12][N:11]=2)=[CH:5][C:4]=1[CH2:24][N:25]([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89655814HCID 89655814, compound

Product 1

HCID 117737506HCID 117737506, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron (202 mg, 3.25 mmol) and concentrated hydrochloric acid (0.02 mL) were added to ethanol/water (6.5 mL/6.5 mL), followed by refluxing for 1 hour. The mixed reaction solution was added with N-(4-chloro-3-((dimethylamino)methyl)phenyl)-6-methyl-5-nitroisoquinolin-1-amine (241.5 mg, 0.65 mmol) obtained in <Step 3> above, followed by refluxing for 1 hour. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with ethanol and chloroform/2-propanol=3/1 (v/v). The resulting filtrate was distilled under reduced pressure, and dissolved in chloroform/2-propanol=3/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (dichloromethane:methanol=9:1 (v/v)) to obtain the title compound (130.9 mg, 59%).

Workup

  1. temperatureby refluxing for 1 hour
  2. customThe mixed reaction solution
  3. customobtained in <Step 3> above,
  4. temperatureby refluxing for 1 hour
  5. filtrationThe reaction mixture was filtered through a Celite pad under reduced pressure
  6. washwashed with ethanol and chloroform/2-propanol=3/1 (v/v)
  7. distillationThe resulting filtrate was distilled under reduced pressure
  8. dissolutiondissolved in chloroform/2-propanol=3/1 (v/v)
  9. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and brine
  10. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe concentrated compound was purified

Sources & evidence

ORD record
ord-2b2ee32930be4b3a951d3860245cd560
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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