Triethylamine → 2-(Pyridin-2-ylmethoxy)-isoindole-1.3-dione

HRID 39305

Reaction equation

HRID 39305 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[OH:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][O:10][N:11]1[C:12](=[O:21])[C:13]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]2[C:15]1=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 122139452-(Pyridin-2-ylmethoxy)-isoindole-1.3-dioneYield 46%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloromethylpyridine hydrochloride (514 mg, 3.13 mmol), N-hydroxyphthalimide (515 mg, 3.18 mmol), and triethylamine (1.3 mL, 9.3 mmol) were mixed in acetonitrile (5 mL) and stirred at 80° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed sequentially with 1N NaOH(aq), water, and brine. The organic phase was dried over MgSO4, filtered, and concentrated. The residue was recrystallized from ethyl acetate and hexanes to provide N-(pyridine-2-ylmethoxy)phthalimide (364 mg, 1.44 mmol).

Workup

  1. washwashed sequentially with 1N NaOH(aq), water, and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-a0c6c07c91f64f5fb80b8604da9ff8f9
Source dataset
uspto-grants-2013_09
Patent number
US08524764B2

Linked notes

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