Water → HCID 9860285, compound

HRID 2185949Notes

Reaction equation

HRID 2185949 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.Cl.[NH2:14][CH:15]1[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[O:22]=[C:16]1[CH:15]([N:14]2[C:8](=[O:9])[C:3]3[C:4](=[CH:10][CH:11]=[CH:12][C:2]=3[CH3:1])[C:5]2=[O:7])[CH2:20][CH2:19][C:18](=[O:21])[NH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 985004-Methyl-1,3-isobenzofurandioneHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 9860285HCID 9860285, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 3-methylphthalic anhydride (2.96 g, 18.2 mmol), 3-aminopiperidine-2,6-dione hydrogen chloride (3.00 g, 18.2 mmol) and sodium acetate (1.57 g, 19.1 mmol) in acetic acid (30 mL) was heated at reflux for 23 hours. The solvent was removed in vacuo to give a solid which was stirred with water (40 mL) for 1 hour, filtered, washed with water (30 mL), and then heated with decolorizing charcoal (1 g) in acetone (2 L) at reflux temperature for 30 min. The suspension was filtered through a pad of Celite to give a clear solution. The solvent of filtrate was removed in vacuo to give 2-(2,6-dioxopiperid-3-yl)-4-methylisoindoline-1,3-dione as a white solid (4.08 g, 82% yield); mp 290.0-292.0° C.; 1H NMR (DMSO-d6); δ2.03-2.09 (m, 1H, CHH), 2.50-2.60 (m, 2H, CH2), 2.63 (s, 3H, CH3), 2.83-2.95 (m, IH, CHH), 5.13 (dd, J=5.4,12.3 Hz, IH, NCH), 7.65-7.79 (m, 3H, Ar), 11.13 (br s, IH, NH); 13C NMR (DMSO-d6) δ17.04, 21.99, 30.93, 48.76, 121.05, 127.89, 131.63, 134.37, 136.91, 137.61, 167.04, 167.83, 169.87, 172.74; Anal Calcd for C14H12N2O4: C, 61.76; H, 4.44; N, 10.29. Found: C, 61.68; H, 4.37; N, 10.17.

Workup

  1. temperatureat reflux for 23 hours
  2. customThe solvent was removed in vacuo
  3. customto give a solid which
  4. filtrationfiltered
  5. washwashed with water (30 mL)
  6. temperatureheated with decolorizing charcoal (1 g) in acetone (2 L)
  7. temperatureat reflux temperature for 30 min
  8. filtrationThe suspension was filtered through a pad of Celite
  9. customto give a clear solution
  10. customThe solvent of filtrate was removed in vacuo

Sources & evidence

ORD record
ord-b81d0cc1c808402d90792a112422ff2a
Source dataset
uspto-grants-2002_06
Patent number
US06403613B1

Reaction notes

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