Phthalic Anhydride → HCID 178514962, compound

HRID 510435Notes

Reaction equation

HRID 510435 reaction equation
[NH2:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[C:5]([OH:16])[NH:4][N:3]=1.[C:17]1(=O)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[O:18]1>C(O)(=O)C>[Cl:15][C:9]1[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][C:6]1[C:5]([OH:16])=[N:4][NH:3][C:2]=1[N:1]1[C:17](=[O:18])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:26]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 178509288HCID 178509288, compound

Product 1

HCID 178514962HCID 178514962, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-amino-4-(2,3-dichlorobenzyl)-1H-pyrazol-5-ol (18 g, 70 mmol) and isobenzofuran-1,3-dione (20 g, 140 mmol) in acetic acid (100 mL), was stirred under reflux for 16 h. The reaction mixture was cooled and filtered to provide the titled compound (13 g, 50%); LC/MS: MS (ES+) m/e 388 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.66 (s, 2H), 7.20-7.31 (m, 2H), 7.51 (d, J=7.5 Hz, 1H), 7.99-8.02 (m, 2H), 8.11 (s, 2H), 8.25-8.28 (m, 2H).

Workup

  1. temperatureunder reflux for 16 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f4a52db312ae4a468c5fb97264e8dcba
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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