Hydrochloric Acid → HCID 178512629, compound

HRID 1067218Notes

Reaction equation

HRID 1067218 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[C:14]2[NH:19][C:20]([NH2:22])=[NH:21])C1C=CC=CC=1.Cl.CO>CCO.[Pd]>[NH3:13].[OH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[C:14]2[NH:19][C:20]([NH2:22])=[NH:21]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 178512628HCID 178512628, compound

Product 2

HCID 222AmmoniaHCID 178512629HCID 178512629, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (5-benzyloxyisoquinolin-1-yl)guanidine (290 mg, 1.0 mmol) in EtOH (10 mL) containing 10% Pd-C (60 mg) and dilute HCl (1.5 mL, 2 M, 3.0 mmol) was stirred under an atmosphere of H2 (4 atmospheres) at 60° C. for 3 d. An additional portion of catalyst (30 mg) and HCl (0.5 mL) were added and hydrogenation continued for a further 3 d. The mixture was filtered through Arbocel with EtOH rinsing, the filtrate was evaporated in vacuo and the residue purified by column chromatography upon silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1 to 84:14:2) as eluant to give (5-hydroxyisoquinolin-1-yl)guanidine (66 mg, 0.33 mmol) as a white solid.

Workup

  1. waithydrogenation continued for a further 3 d
  2. filtrationThe mixture was filtered through Arbocel with EtOH rinsing
  3. customthe filtrate was evaporated in vacuo
  4. customthe residue purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-eaecc7dfb31947f68868f9b8e11fb007
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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