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Acetic Acid → 1H-Isoindole-1,3(2H)-dione, 4-nitro-2-(3-pyridinylmethyl)-

HRID 1609583
Notes
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Reaction equation

HRID 1609583 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].C(O)(=O)C.[NH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:5]=1[C:10](=[O:11])[N:19]([CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[C:7]2=[O:9])([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 216313-Nitrophthalic anhydrideHCID 310183-Pyridinemethanamine

Product 1

HCID 110005281H-Isoindole-1,3(2H)-dione, 4-nitro-2-(3-pyridinylmethyl)-Yield 93.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 15.0 g of 3-nitrophthalic acid anhydride, 233 ml of acetic acid and 80 ml of toluene was added 10.1 g of 3-aminomethylpyridine, and the resultant mixture was refluxed for 1.5 hours under heating. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate, washed with 1N aqueous sodium hydroxide and water in order, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 20.6 g of the titled compound.

Workup

  1. temperatureunder heating
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. washwashed with 1N aqueous sodium hydroxide and water in order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8b0e9d58bd649efb6b6cdb05b3e4963
Source dataset
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05401756

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes