Water → HCID 66958389, compound

HRID 1984517Notes

Reaction equation

HRID 1984517 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([C:19]([O:21]CC)=[O:20])[CH:14]=1.O>Cl.C(O)(=O)C>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=1

Participants

5

Reactant 2

HCID 962WaterHCID 66958716HCID 66958716, compound

Product 1

HCID 66958389HCID 66958389, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-methyl-1H-pyrazole-3-carboxylate (8.13 g, 25.9 mmol) in hydrochloric acid (33 mL of 1 M) and acetic acid (33 mL) was heated at reflux intermittently for six hours and allowed to cool to room temperature; a precipitate formed. Water was added, and the solid was isolated by filtration, washed with water, and dried on the vacuum filter funnel for two days to provide 3.79 g of 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-methyl-1H-pyrazole-3-carboxylic acid as a brown solid.

Workup

  1. temperatureat reflux intermittently for six hours
  2. customa precipitate formed
  3. customthe solid was isolated by filtration
  4. washwashed with water
  5. customdried on the vacuum
  6. filtrationfilter funnel for two days

Sources & evidence

ORD record
ord-9f319ac1a0c04edeb932e96eeb13b711
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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