3-Nitrophthalic anhydride → HCID 22241217, compound

HRID 891985Notes

Reaction equation

HRID 891985 reaction equation
[O:1]=[C:2]1[CH:7]([NH:8][C:9]([O:11]CC2C=CC=CC=2)=O)[CH2:6][CH:5]([O:19][C:20](=[O:22])[CH3:21])[C:4](=[O:23])[NH:3]1.[N+:24]([C:27]1[CH:37]=[CH:36][CH:35]=[C:29]2C([O:32][C:33](=O)[C:28]=12)=O)([O-:26])=[O:25]>C(O)(=O)C.[Pd]>[N+:24]([C:27]1[CH:37]=[CH:36][CH:35]=[C:29]2[C:28]=1[C:33](=[O:32])[N:8]([CH:7]1[CH2:6][CH:5]([O:19][C:20](=[O:22])[CH3:21])[C:4](=[O:23])[NH:3][C:2]1=[O:1])[C:9]2=[O:11])([O-:26])=[O:25]

Participants

5

Reactant 2

HCID 216313-Nitrophthalic anhydrideHCID 12047333HCID 12047333, compound

Product 1

HCID 22241217HCID 22241217, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2,6-dioxo-3-benzyloxycarbonylamino-5-acetoxypiperidine (9 g, 28.2 mmol) and Pd/C (10%, 0.9 g) in acetic acid (90 mL) is shaken under hydrogen (50–60 psi) for 3 hours. The suspension is filtered through a pad of Celite and washed with acetic acid. To the filtrate is added 3-nitrophthalic anhydride (5.4 g, 28.2 mmol), this mixture is heated at reflux for 18 hours, and the solvent is then removed in vacuo to give 3-(4-nitro-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine which can be further purified by column chromatography.

Workup

  1. filtrationThe suspension is filtered through a pad of Celite
  2. washwashed with acetic acid
  3. temperaturethis mixture is heated
  4. temperatureat reflux for 18 hours
  5. customthe solvent is then removed in vacuo

Sources & evidence

ORD record
ord-4e1f0d9298a34a5583981bdc04314eb4
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

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