Water → HCID 9860285, compound

HRID 1162182Notes

Reaction equation

HRID 1162182 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); δ 2.03-2.09 (m, 1H, CHH), 2.50-2.60 (m, 2H, CH2), 2.63 (s, 3H, CH3), 2.83-2.95 (m, 1H, CHH), 5.13 (dd, J=5.4, 12.3 Hz, 1H, NCH), 7.65-7.79 (m, 3H, Ar), 11.13 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 17.04, 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-437cc019c7d04ea6aea29615a66cb348
Source dataset
uspto-grants-2010_10
Patent number
US07820697B2

Reaction notes

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