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Sodium Iodide → 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

HRID 506971
Notes
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Reaction equation

HRID 506971 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1.Cl.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH-].[Na+]>CC(C)=O>[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 670185873-(7-hydroxy-1-oxo-1H-isoquinolin-2-yl)-4-methylbenzoic acid

Product 1

HCID 67018579
3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid
Yield 39.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-(7-Hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (0.47 g), 2-dimethylaminoethyl chloride hydrochloride (0.69 g), potassium carbonate (2.21 g), and sodium iodide (24 mg) were stirred in acetone (25 ml) at 60° C. for 17 hours. 2N NaOH (5 ml) was added, the reaction stirred for 20 minutes and the acetone removed by evaporation. The residue was acidified with concentrated hydrochloric acid and the solution was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to give 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as an oil (232 mg); Mass Spectrum: M+H+ 367.

Workup

  1. customthe acetone removed by evaporation
  2. customthe solution was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  3. additiona 99:1 mixture of methanol and aqueous ammonia solution

Sources & evidence

ORD record
ord-f3edd1e983664c16b0a39fbb47792d7a
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