4-Hydrazinobenzoic acid → 4-(3,5-dimethyl-1H-pyrazol-1-yl)benzoic acid

HRID 252851Notes

Reaction equation

HRID 252851 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].[CH3:12][C:13](=O)[CH2:14][C:15](=O)[CH3:16]>C(O)(C)C>[CH3:12][C:13]1[CH:14]=[C:15]([CH3:16])[N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[N:2]=1

Participants

4

Reactant 2

HCID 120894-Hydrazinobenzoic acidHCID 31261Acetylacetone

Product 1

HCID 6932064-(3,5-dimethyl-1H-pyrazol-1-yl)benzoic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Hydrazinylbenzoic acid (251a, 2 g, 13.2 mmol) and pentane-2,4-dione (1.35 mL, 13.2 mmol) were dissolved in isopropanol (40 mL) and refluxed for 15 hours. The solvent was removed under reduced pressure to afford 252a as a white solid (2.85 g, 99% yield). 1H NMR: (DMSO) δ 8.04 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.8 Hz, 2H), 6.14 (s, 1H), 2.39 (s, 3H), 2.22 (s, 3H).

Workup

  1. temperaturerefluxed for 15 hours
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-57f635c42bac416b894d346964ab70e9
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

Loading…