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N-Hydroxyphthalimide → HCID 59479004, compound

HRID 450750
Notes
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Reaction equation

HRID 450750 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

HCID 59479004HCID 59479004, compoundYield 47.7%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 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-isoindo1-2-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-48ecb43fee3442588cdae7b0ac209325
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486970B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes