Triethylamine → HCID 67111066, compound

HRID 540750Notes

Reaction equation

HRID 540750 reaction equation
C(O)(=O)C(O)=O.[CH2:7]([NH:9][NH2:10])[CH3:8].[C:11]([C:13]1[CH:14]=[C:15]([C:19]#[C:20][C:21](OCC)=[O:22])[CH:16]=[CH:17][CH:18]=1)#[N:12].C(N(CC)CC)C>C(O)C>[CH2:7]([N:9]1[C:19]([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[C:11]#[N:12])=[CH:20][C:21](=[O:22])[NH:10]1)[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 18549368HCID 18549368, compound

Product 1

HCID 67111066HCID 67111066, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl hydrazine oxalate (4.01 g, 26.7 mmol, 1.50 equiv) was added to a solution of ethyl 3-(3-cyanophenyl)prop-2-ynoate (3.55 g, 17.8 mmol, 1 equiv) and triethylamine (3.73 mL, 26.7 mmol, 1.50 equiv) in ethanol (180 mL). The reaction mixture was heated to 80° C. for 3.5 hours, then cooled to 22° C. The cooled reaction mixture was concentrated by rotary evaporation, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated to afford 3-(2-ethyl-5-oxo-2,5-dihydro-1H-pyrazol-3-yl)benzonitrile (3.5 g, 3:1 mixture of regioisomers in favor of desired product). The mixture of regioisomers was used without separating in the next step. Calcd (M+1)+: 214.1. Found: 214.1.

Workup

  1. temperaturecooled to 22° C
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated by rotary evaporation
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialthe washed solution was dried over sodium sulfate
  7. filtrationThe dried solution was filtered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c53d08ca44f7420fa39ea236206f43ad
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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