Sodium Bicarbonate → Methyl 2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)acetate

HRID 571243

Reaction equation

HRID 571243 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=[O:12])[N:6]([CH2:13][C:14]([OH:16])=[O:15])[C:5]2=[O:17].[C:18]([O-])(O)=O.[Na+]>CO.OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=[O:12])[N:6]([CH2:13][C:14]([O:16][CH3:18])=[O:15])[C:5]2=[O:17]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 7123142-(5,6-dichloro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

Product 1

HCID 3710015Methyl 2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)acetateYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)acetic acid (2.33 g, 8.50 mmol) in MeOH (35 ml), conc. H2SO4 (3 ml) was added at 0° C. The reaction was warmed at room temperature and stirred for 16 hours. The mixture was poured into an ice/water mixture and neutralized with aqueous NaHCO3. The resulting precipitate was recovered by filtration, washed with water and dried affording methyl 2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)acetate (2.42 g, 8.40 mmol, 99% yield). MS/ESI+ 288.0 [MH]+.

Workup

  1. filtrationThe resulting precipitate was recovered by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-93691b2c47a841858b2ba49395280e70
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Linked notes

Loading…