Acetic Acid → HCID 178514959, compound

HRID 1951290Notes

Reaction equation

HRID 1951290 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([OH:7])[NH:4][N:3]=1.[C:8]1(=O)[O:13][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.C(O)(=O)C>C1COCC1>[OH:7][C:5]1[NH:4][N:3]=[C:2]([N:1]2[C:11](=[O:12])[C:10]3[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]2=[O:13])[CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6811Phthalic AnhydrideHCID 962215-Amino-1H-pyrazol-3-ol

Product 1

HCID 178514959HCID 178514959, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-amino-1H-pyrazol-5-ol (10.00 g, 101 mmol) in THF (300 mL) at RT was added phthalic acid anhydride (14.9 g, 101 mmol) followed by acetic acid (69.3 ml, 1.21 mol). The mixture was heated to reflux. After 4 days, the mixture was concentrated in vacuo to afford a slurry that was cooled to 0° C. and filtered. The solid was rinsed with Et2O and dried in vacuo to afford 2-(5-hydroxy-1H-pyrazol-3-yl)isoindoline-1,3-dione as a yellow solid that was advanced without further purification. MS: Found M+H+=230.2.

Workup

  1. temperatureThe mixture was heated to reflux
  2. concentrationthe mixture was concentrated in vacuo
  3. customto afford a slurry that
  4. filtrationfiltered
  5. washThe solid was rinsed with Et2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2c128b4fcd084ed586a683b37ed74654
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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