Ammonia → Ethyl 5-(propan-2-yl)-1H-pyrazole-3-carboxylate

HRID 1827954Notes

Reaction equation

HRID 1827954 reaction equation
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1)([CH3:3])[CH3:2].O.N.[CH2:14](O)[CH3:15]>S(=O)(=O)(O)O>[CH2:14]([O:10][C:9]([C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[NH:8][N:7]=1)=[O:11])[CH3:15]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 7764215-(propan-2-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 6422484Ethyl 5-(propan-2-yl)-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-Isopropyl-1H-pyrazole-3-carboxylic acid (WO 03/035065, page. 485, example 17b) (1.00 g, 6.49 mmol) was dissolved in a mixture of concentrated sulphuric acid (1.5 mL) and ethanol (25 mL) and the reaction mixture heated at reflux for 3 hours. The reaction mixture was cooled, poured into water, basified with 0.88 ammonia then extracted with ethyl acetate. The ethyl acetate was washed with brine, dried over magnesium sulphate and concentrated in vacuo to yield the title product, 514 mg (43%).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionthen extracted with ethyl acetate
  5. washThe ethyl acetate was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5456da4cd07443dd9ae26f4f0434d1ff
Source dataset
uspto-grants-2006_06
Patent number
US07056934B2

Reaction notes

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