Tetrahydrofuran → HCID 66854396, compound

HRID 251948

Reaction equation

HRID 251948 reaction equation
CON=[C:4]([CH2:10][C:11](=O)[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:14][C:15]1[C:16]([NH:21][NH2:22])=[N:17][CH:18]=[CH:19][CH:20]=1.O1CCCC1>C(O)(=O)C>[Cl:14][C:15]1[C:16]([N:21]2[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][C:11]([CH3:12])=[N:22]2)=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5561003-Chloro-2-hydrazinylpyridineHCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoate

Product 1

HCID 66854396HCID 66854396, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.34 g of ethyl 2-methoxyimino-4-oxopentanoate, 1.23 g of 3-chloro-2-hydrazinopyridine, 25 ml of tetrahydrofuran and 50 ml of acetic acid was heated to reflux for 8 hours. The reaction mixture was concentrated under reduced pressure. Water was poured into the residue, and the mixture was extracted with methyl t-butyl ether two times. The combined organic layer was washed successively with a 1N aqueous sodium hydroxide solution, water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.30 g of ethyl 1-(3-chloro-2-pyridinyl)-3-methyl-1H-pyrazole-5-carboxylate of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was poured into the residue
  5. extractionthe mixture was extracted with methyl t-butyl ether two times
  6. washThe combined organic layer was washed successively with a 1N aqueous sodium hydroxide solution, water
  7. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04d72ddb2c814fd4aaed7d240b7cce25
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Linked notes

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