N-Hydroxyphthalimide → 2-(5-Bromo-pyridin-2-ylmethoxy)-isoindole-1,3-dione

HRID 1039539Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9]Cl)=[N:7][CH:8]=1.[OH:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].C(N(CC)C(C)C)(C)C>C(#N)C.O>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:11][N:12]2[C:16](=[O:17])[C:15]3[C:14](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]2=[O:22])=[N:7][CH:8]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of 5-Bromo-2-chloromethyl-pyridine hydrochloride (63.7 g, 0.262 mol) and N-hydroxylphthalimide (64 g, 0.393 mol) in acetonitrile (400 mL) was placed in water bath and added N,N-diisopropylethylamine (182 mL, 1.05 mol) using dropping funnel for 10 min. It was heated at 65° C. for 4 hrs and evaporated off the solvent and extra base. Then, water (100 mL) was added to the reaction mixture and stirred for overnight. The resulting solid was filtered, washed with water (2×50 mL) and acetonitrile (100 mL). The white solid was dried on vacuum pump to provide the title compound (84.2 g, 84%) as a white solid. MS-ESI m/z 334.95 (M+H)+.

Workup

customfor 10 min
customevaporated off the solvent and extra base
additionThen, water (100 mL) was added to the reaction mixture
filtrationThe resulting solid was filtered
washwashed with water (2×50 mL) and acetonitrile (100 mL)
customThe white solid was dried on vacuum pump

Sources & evidence

ORD record: ord-308d4370c26e4744a0e98d01ea3655b9
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552162B2

Reaction notes

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