Ammonia → 1-Amino-3,4-dihydro-7-methoxyisoquinoline

HRID 1704808Notes

Reaction equation

HRID 1704808 reaction equation
FS([O-])(=O)=O.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][NH+:14]=[C:15]2SC)=[CH:10][CH:9]=1.[NH3:20]>C(O)C>[NH2:20][C:15]1[C:16]2[C:11](=[CH:10][CH:9]=[C:8]([O:7][CH3:6])[CH:17]=2)[CH2:12][CH2:13][N:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 867361803,4-Dihydro-7-methoxy-1-methylthioisoquinolinium fluorosulfonate

Product 1

HCID 187859341-Amino-3,4-dihydro-7-methoxyisoquinolineYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dihydro-7-methoxy-1-methylthioisoquinolinium fluorosulfonate (10.0 g., 0.0362 mole) was added to ethanol (100 ml.) which was saturated with ammonia in a steel bomb. The stirred mixture was heated on a steam bath for 2 hours. The mixture was combined with material from four similar runs andd flash evaporated to dryness. The residue was partitioned between 5N NaOH (300 ml.) and methylene chloride. The organic layer was washed with water (2×) and dried with sodium sulfate. The solid obtained after removal of the methylene chloride was recrystallized from benzene to give 23 g. (72% yield) of 1-amino-3,4-dihydro-7-methoxyisoquinoline, m.p. 114°-117.5°. Recrystallization from ethyl acetate afforded the analytical sample, m.p. 117.5°-119.5°.

Workup

  1. temperatureThe stirred mixture was heated on a steam bath for 2 hours
  2. customevaporated to dryness
  3. customThe residue was partitioned between 5N NaOH (300 ml.) and methylene chloride
  4. washThe organic layer was washed with water (2×)
  5. dry with materialdried with sodium sulfate
  6. customThe solid obtained
  7. customafter removal of the methylene chloride
  8. customwas recrystallized from benzene
  9. customto give 23 g

Sources & evidence

ORD record
ord-2bf77cd1c9b049a8922464f8c9779ed6
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

Loading…