Hydrochloric Acid → HCID 18176282, compound

HRID 651608Notes

Reaction equation

HRID 651608 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH2:13])=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl.[C:15](=N)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO.ClCCCl>[C:15](=[N:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[CH3:12])[C:2]([Cl:1])=[N:3][CH:4]=[CH:5]2)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 53811061HCID 53811061, compound

Product 1

HCID 18176282HCID 18176282, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-chloro-7-methyl-isoquinolin-6-ylamine (0.1 g, 0.52 mmol) in MeOH (5 mL) at 0° C. is bubbled HCl gas for 1 minute, then the solvent is removed in vacuo. The remaining white solid is diluted with 1,2 dichloroethane and benzophenone imine (0.15 mL, 0.89 mmol) is added. The resulting suspension is heated to reflux for 48 hours, then cooled to room temperature and concentrated to dryness. The crude material is diluted with CH2Cl2 and washed with saturated NaHCO3 solution and brine. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography using 10% EtOAc/hexanes as the eluent to afford the title compound (0.159 g, 0.45 mmol) as a yellow oil.

Workup

  1. customthe solvent is removed in vacuo
  2. additionis added
  3. temperatureThe resulting suspension is heated
  4. temperatureto reflux for 48 hours
  5. concentrationconcentrated to dryness
  6. additionThe crude material is diluted with CH2Cl2
  7. washwashed with saturated NaHCO3 solution and brine
  8. dry with materialThe organic layer is dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-41cbdacde8aa4cfea3d19a0d104e2ab3
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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