Pyridine → HCID 9992083, compound

HRID 1783306Notes

Reaction equation

HRID 1783306 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.[CH3:14][N:15]([CH3:20])[CH2:16][C:17](O)=[O:18].N1C=CC=CC=1.[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[NH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[C:10]([C:11]=1[C:17](=[O:18])[CH2:16][N:15]([CH3:20])[CH3:14])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

8

Reactant 4

HCID 1049PyridineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 122275235597-05-7

Product 1

HCID 9992083HCID 9992083, compoundYield 39.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3-Amino-2H-isoquinolin-1-one (9.0 g), dimethylglycine hydrochloride (10.2 g) and pyridine (22.7 mL) were suspended in methylene chloride (100 mL), and 2-chloro-1,3-dimethylimidazolinium chloride (12.4 g) was added under ice-cooling. Then the mixture was stirred at room temperature for 2 hrs. After the completion of the reaction, the reaction mixture was dissolved in a mixed solvent (chloroform and lo methanol 10:1), washed with aqueous potassium carbonate solution and the organic layer was dried over magnesium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography. The fraction eluted with chloroform:methanol was concentrated, and the precipitated crystals were collected by filtration to give 3-amino-4-(2-(dimethylamino) acetyl)-2H-isoquinolin-1-one (5.5 g). This compound was dissolved in chloroform-methanol mixed solvent, and 4N hydrogen chloride-dioxane was added. The precipitated crystals were collected by filtration, and recrystallized from ethanol-water mixed solvent to give 3-amino-4-(2-(dimethylamino)acetyl)-2H-isoquinolin-1-one hydrochloride monohydrate (4.5 g).

Workup

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. washwashed with aqueous potassium carbonate solution
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography
  7. washThe fraction eluted with chloroform
  8. concentrationmethanol was concentrated
  9. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-51deee21f82a43f0bff6a58bf56afe54
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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