Ammonia → 1-Isoquinolinamine, 7-methoxy-

HRID 2304297Notes

Reaction equation

HRID 2304297 reaction equation
[NH3:1].Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH:6]=[CH:5][N:4]=1>C(O)C>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[CH:5][N:4]=[C:3]2[NH2:1])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 222501811-Chloro-7-methoxyisoquinoline

Product 1

HCID 226656441-Isoquinolinamine, 7-methoxy-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

Liquid ammonia (220 mL) was added to a solution of 32.8 g of 1-chloro-7-methoxy-isoquinoline in 420 mL of ethanol in a steel vessel. Nitrogen was pressed upon until an initial pressure of 20 atm. was obtained. This reaction mixture was heated for 2 days at 170° C. The solvent was removed in vacuo and the residue dissolved in water. The pH value was adjusted to pH 10 by adding aqueous sodium carbonate solution, followed by extraction with ethyl acetate. The organic extract was washed with brine and dried (Na2SO4). Evaporation of the solvent in vacuo gave pure 7-methoxy-isoquinolin-1-ylamine as a white solid. Yield 24.0 g (81%); m.p. 128-130° C.

Workup

  1. customwas obtained
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in water
  4. additionby adding aqueous sodium carbonate solution
  5. extractionfollowed by extraction with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-139963d917a54e96a5caee816c1a30cd
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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