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Sodium Iodide → 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide

HRID 506973
Notes
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Reaction equation

HRID 506973 reaction equation
[CH2:1]([NH:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=3)[C:13]2=[O:23])[CH:6]=1)[CH3:2].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[CH:21][N:12]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=3[CH3:11])[C:4]([NH:3][CH2:1][CH3:2])=[O:24])[C:13]2=[O:23])=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 11674186N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Product 1

HCID 116325883-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (88 mg), 2-dimethylaminoethyl chloride hydrochloride (51 mg), potassium carbonate (0.38 g), and sodium iodide (3 mg) were stirred in acetone (4 ml) at 60° C. for 17 hours. The reaction mixture was filtered, the solids washed with acetone, and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 2N NaOH solution, brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica-column eluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution gave 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide as a white solid; NMR Spectrum: (DMSOd6) 1.11 (t, 3H), 2.10 (s, 3H), 2.24 (s, 6H), 2.68 (t, 2H), 3.28 (m, 2H), 4.18 (m, 2H), 6.72 (d, 1H), 7.21 (d, 1H), 7.41 (d, 1H), 7.50 (d, 1H), 7.69 (s, 1H), 7.71 (d, 1H), 7.78 (s, 1H), 7.89 (d, 1H), 8.48 (s, 1H); Mass Spectrum: M+H+ 394.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed with acetone
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 2N NaOH solution, brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customPurification by column chromatography on a silica-column
  9. washeluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution

Sources & evidence

ORD record
ord-714e12ab53134fe0bbe96d938569dd17
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786115B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes