Pyridine → 2-(4-methoxyphenyl)-3-methyl-1(2H)-isoquinolinone

HRID 2386950Notes

Reaction equation

HRID 2386950 reaction equation
O=[C:2]([CH3:13])[CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O.[CH3:14][O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C.N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:14][O:15][C:16]1[CH:22]=[CH:21][C:19]([N:20]2[C:2]([CH3:13])=[CH:3][C:4]3[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:6]2=[O:8])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7732P-AnisidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110739652-(2-oxopropyl)benzoic Acid

Product 1

HCID 231511792-(4-methoxyphenyl)-3-methyl-1(2H)-isoquinolinoneYield 44.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-(2-oxopropyl)benzoic acid (100 mg, 0.56 mmol), 4-methoxyaniline (76 mg, 0.56 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.84 mmol) and pyridine (0.5 mL) were dissolved in chloroform (5 mL) and stirred at room temperature overnight. Chloroform was added, the organic phase was washed by aqueous citric acid solution, sodium hydrogen carbonate aqueous solution and saturated brine in that order, and dried with anhydrous sodium sulfate. The product was purified by silica gel column chromatography (hexane/ethyl acetate=10/0-3/7) to obtain the target compound (66 mg, 44%) as a light brown solid.

Workup

  1. washthe organic phase was washed by aqueous citric acid solution, sodium hydrogen carbonate aqueous solution and saturated brine in that order
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe product was purified by silica gel column chromatography (hexane/ethyl acetate=10/0-3/7)

Sources & evidence

ORD record
ord-a1d1328edbfd407e870bcefe12265a31
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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