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Hydrochloric Acid → 2-(Methyl-3-nitro-benzyl)-isoindole-1,3-dione

HRID 1071528
Notes
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Reaction equation

HRID 1071528 reaction equation
C[C:2]1[CH:13]=[CH:12][C:5]([CH2:6]OS(C)(=O)=O)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH3:17]N(C=O)C.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K].Cl>CCCCCC.C(OCC)(=O)C>[CH3:17][CH:6]([N:26]1[C:22](=[O:32])[C:23]2[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:25]1=[O:27])[C:5]1[CH:12]=[CH:13][CH:2]=[C:3]([N+:14]([O-:16])=[O:15])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 208002884-Methyl-3-nitrobenzyl methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 223935242-(Methyl-3-nitro-benzyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 21226206
Ethyl acetate hexane
Solvent

Conditions

Temperature
60 °C

Procedure

Methanesulfonic acid 4-methyl-3-nitro-benzyl ester (0.45 g, 1.83 mmol) was added to anhydrous DMF (20 mL), under argon, and potassium phthalimide (0.34 g, 1.83 mmol) was added. The reaction mixture was heated to 60° C. for 12 h. The reaction mixture was cooled and poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (4:1 hexane/ethyl acetate) Yield 0.45 g. 1H NMR (CDCl3, 300 MHz): δ 2.58 (s, 3H), 4.88 (s, 2H), 7.30 (d, J=7 Hz, 1H), 7.57 (d, J=7 Hz, 1H), 7.24-7.77 (m, 2H), 7.84-7.89 (m, 2H), 8.02 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-d20e26f96fa74045a2cd41d8a52b0b07
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06906067B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes