Acetic Acid → 4-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamine

HRID 2183545

Reaction equation

HRID 2183545 reaction equation
O=[CH:2][CH:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])[C:4]#[N:5].O.[NH2:16][NH2:17].C(O)(=O)C.Cl>C1C=CC=CC=1.O>[CH3:14][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[C:6]=1[C:3]1[CH:2]=[N:17][NH:16][C:4]=1[NH2:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 224743973-Oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile

Product 1

HCID 224743864-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamineYield 10.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 3-oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile (2.300 g, 12.3 mmol), hydrazine hydrate (0.93 g) and glacial acetic acid (1.55 ml) in 20 ml benzene was heated at reflux for 4.5 hours. Reaction mixture was cooled to room temperature and 50 ml of 18.5% HCl in water was added. The benzene layer was separated and reextracted with 18.5% HCl. The aqueous layer were combined and neutralized with ammonium hydroxide and stirred at rt. overnight. Precipitate formed and was filtered to yield the title compound (0.256 g) as a yellow solid. The benzene layer was concentrated and purified through silica gel column using 5% methanol in chloroform as eluent to give an additional 1.450 g of the title compound; 1H NMR (CDCl3) ä 7.24(s, 1H), 6.95(s, 2H), 4.75(brs, 2H), 2.32(s, 3H), 2.13(s, 6H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customReaction mixture
  4. customThe benzene layer was separated
  5. customovernight
  6. customPrecipitate formed
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-9b402513c4384f52b727e614cf322e46
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Linked notes

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