Water → HCID 66958619, compound

HRID 1984395Notes

Reaction equation

HRID 1984395 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][CH2:13][C:14]1[N:18]([CH2:19][CH2:20][CH3:21])[N:17]=[C:16]([C:22]([O:24]CC)=[O:23])[CH:15]=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][CH2:13][C:14]1[N:18]([CH2:19][CH2:20][CH3:21])[N:17]=[C:16]([C:22]([OH:24])=[O:23])[CH:15]=1

Participants

5

Reactant 2

HCID 962WaterHCID 66959074HCID 66959074, compound

Product 1

HCID 66958619HCID 66958619, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

A stirred solution of ethyl 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-propyl-1H-pyrazole-3-carboxylate (45.1 g, 127 mmol) in 1 M aqueous hydrochloric acid (157 mL) and acetic acid (157 mL) was heated at 95° C. (internal temperature) for 10 hours and then cooled to 10° C. Water (300 mL) was added and a white solid was isolated by filtration, washed with water and diethyl ether, and dried. The solid was treated with toluene (150 mL) and heated at reflux for 3 hours with a Dean-Stark trap. The mixture was cooled in an ice bath to 10° C. and a solid was isolated by filtration and dried to provide 28.85 g of 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-propyl-1H-pyrazole-3-carboxylic acid.

Workup

  1. customa white solid was isolated by filtration
  2. washwashed with water and diethyl ether
  3. customdried
  4. additionThe solid was treated with toluene (150 mL)
  5. temperatureheated
  6. temperatureat reflux for 3 hours with a Dean-Stark trap
  7. temperatureThe mixture was cooled in an ice bath to 10° C.
  8. customa solid was isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-67a4aeff317d41a0937950c36ffcdcf4
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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