Methanesulfonic Acid → HCID 86710684, compound

HRID 1027270Notes

Reaction equation

HRID 1027270 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]3[CH:17]=[N:16][CH:15]=[C:12]32)=[CH:7][C:6]=1[O:18][CH3:19])(C)C.CS(O)(=O)=O>C(Cl)(Cl)Cl>[CH3:19][O:18][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[OH:4])[C:12]1=[CH:15][N:16]=[CH:17][N:11]1[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59626590HCID 59626590, compound

Product 1

HCID 86710684HCID 86710684, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
63 °C

Procedure

To a 50 mL round bottom flask was added 9-isopropoxy-8-methoxy-5,6-dihydroimidazo[5,1-a]isoquinoline (180 mg, 0.70 mmol), chloroform (13 mL), and methanesulfonic acid (1.3 mL, 20.02 mmol). The resulting mixture was heated at 63° C. for 2 h then cooled to RT and concentrated in vacuo. To the resulting oil was added H2O and aqueous saturated sodium carbonate. The solution was extracted with EtOAc (2×), and the organic extracts were combined, dried with sodium sulfate and concentrated in vacuo to afford 8-methoxy-5,6-dihydroimidazo[5,1-a]isoquinolin-9-ol. (151 mg) MS [M+H+]=217.4.

Workup

  1. temperaturethen cooled to RT
  2. concentrationconcentrated in vacuo
  3. additionTo the resulting oil was added H2O and aqueous saturated sodium carbonate
  4. extractionThe solution was extracted with EtOAc (2×)
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7f1cc85b352434db8cb6d1c83478d4b
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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