N-Hydroxyphthalimide → HCID 59479004, compound

HRID 1747027Notes

Reaction equation

HRID 1747027 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:32]1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O.C(OCC)(=O)C.C1COCC1>[O:42]=[C:33]1[C:34]2[C:35](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36](=[O:37])[N:32]1[O:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][N:4]=1

Participants

8

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 450843336-(Hydroxymethyl)pyridine-3-carboxamide

Product 1

HCID 59479004HCID 59479004, compoundYield 47.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 313 mg of 6-(hydroxymethyl)nicotinamide, 540 mg of triphenylphosphine, 503 mg of N-hydroxyphthalimide, and 4.7 ml of THF was added dropwise 0.53 ml of diisopropyl azodicarboxylate, followed by stirring overnight. After concentration, the solid thus produced was suspended in water, and ethyl acetate was added thereto. After stirring for 30 minutes, the solid was collected by filtration to obtain 292 mg of 6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}nicotinamide.

Workup

  1. concentrationAfter concentration
  2. customthe solid thus produced
  3. stirringAfter stirring for 30 minutes
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-e0a75b92906d450e9ab849c03d84d934
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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