Triethylamine → 4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol

HRID 508448Notes

Reaction equation

HRID 508448 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[CH:6][C:5]2=O.S(O)(O)(=O)=O.[CH3:18][NH:19][NH2:20].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:8])=[C:4]([C:5]2[N:19]([CH3:18])[N:20]=[CH:7][CH:6]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 165286Methylhydrazine sulfateHCID 6019896-Chlorochromone

Product 1

HCID 1355532144-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6-chlorochromone (2.00 g, 0.011 mol) in ethanol (35 mL) was added methylhydrazine sulfate (1.85 g, 0.013 mol) and triethylamine (2.0 mL, 0.014 mol) and the mixture was heated at reflux for 18 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the resulting residue purified by silica gel chromatography eluting with 0 to 100% EtOAc in hexane to yield two regioisomeric products in a 1:4 ratio, the title compound being the minor regiosiomer.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe resulting residue purified by silica gel chromatography
  5. washeluting with 0 to 100% EtOAc in hexane
  6. customto yield two regioisomeric products in a 1:4 ratio

Sources & evidence

ORD record
ord-d1c1bf1b29ce420f8d758011b46d8eb2
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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