N-Hydroxyphthalimide → HCID 69011018, compound

HRID 594176Notes

Reaction equation

HRID 594176 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

6

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 81531DiisopropylethylamineHCID 534382005-Bromo-2-(chloromethyl)pyridine hydrochloride

Product 1

HCID 69011018HCID 69011018, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

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

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

Sources & evidence

ORD record
ord-98b27e90719649be815003a0f810ae0b
Source dataset
uspto-grants-2016_01
Patent number
US09242974B2

Reaction notes

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