N-Carbethoxyphthalimide → 2-[2-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1033022Notes

Reaction equation

HRID 1033022 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][C:6]([CH2:12][CH3:13])=[C:5]([CH3:14])[N:4]=1.C(N1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])(OCC)=O>C(O)C>[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][N:11]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])=[CH:7][C:6]([CH2:12][CH3:13])=[C:5]([CH3:14])[N:4]=1

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 103977473-Pyridineethanamine,5-ethyl-2-methoxy-6-methyl-

Product 1

HCID 4642742-[2-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dioneYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude 2-methoxy-3-(2-aminoethyl)-5-ethyl-6-methylpyridine (332 mg) in ethanol (7 mL) was added N-(carbethoxy) phthalimide (406 mg, 1.85 mmol). After stirring at ambient temperature for three hours the solvent was evaporated and the residue was chromatographed on silica gel by gradient elution with 20-100% ethyl acetate/hexane. The appropriate fractions were combined, the solvent evaporated and the residue triturated with hexane as the product slowly crystallized out to yield 202 mg of pure product, m.p. 77°-79° C.

Workup

  1. customwas evaporated
  2. customthe residue was chromatographed on silica gel by gradient elution with 20-100% ethyl acetate/hexane
  3. customthe solvent evaporated
  4. customthe residue triturated with hexane as the product
  5. customslowly crystallized out

Sources & evidence

ORD record
ord-b843df371b2541ecb41930809a340c2d
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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