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

HRID 336046Notes

Reaction equation

HRID 336046 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-5c90fc03d9424bd78d9d45bb260a30a2
Source dataset
uspto-grants-2014_11
Patent number
US08884030B2

Reaction notes

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