Potassium Hydroxide → 6-Aminobenzothieno[3,2-h]Isoquinoline

HRID 21541Notes

Reaction equation

HRID 21541 reaction equation
C([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=13)[CH:13]=[N:12][CH:11]=[CH:10]2)(OCC)=O.[OH-].[K+]>C(O)C.O>[NH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=13)[CH:13]=[N:12][CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 3012116-Carbethoxyaminobenzothieno[3,2-h]isoquinoline

Product 1

HCID 3019236-Aminobenzothieno[3,2-h]IsoquinolineYield 103%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Two hundred mg (0.62 mM) of 6-carbethoxyaminobenzothieno[3,2-h]isoquinoline (9), prepared in the preceding Example, was added to a solution of 2 g KOH in 5 ml ethanol and 2 ml water. Two layers formed. The mixture was stirred and heated at reflux for approximately 2-3 hr. A yellow solid separated after about an hour, and was collected via filtration and air dried to give 160 mg product, m.p. 220° C.-225° C. This initial product was recrystallized twice from a mixture of DMF and water to provide 120 mg final product, m.p. 223.5° C.-224.5° C., which was then characterized via I.R. and mass spectrometry as compound 10.

Workup

  1. customTwo layers formed
  2. temperatureheated
  3. temperatureat reflux for approximately 2-3 hr
  4. customA yellow solid separated after about an hour
  5. filtrationwas collected via filtration and air
  6. customdried

Sources & evidence

ORD record
ord-dfe888c2a2ea4c15bdff73fa9e7ebe00
Source dataset
uspto-grants-1995_06
Patent number
US05424315

Reaction notes

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