Triethylamine → 3-(1-ethyl-5-oxo-2,5-dihydro-1H-pyrazol-3-yl)benzonitrile

HRID 540746Notes

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](=O)[CH2:20][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:21](=[O:22])[CH:20]=[C:19]([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[C:11]#[N:12])[NH:10]1)[CH3:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl hydrazine oxalate (15.6 g, 104 mmol, 1.50 equiv) was added to a solution of ethyl 3-(3-cyanophenyl)-3-oxopropanoate (15.0 g, 69.1 mmol, 1 equiv) and triethylamine (14.4 mL, 104 mmol, 1.50 equiv) in ethanol (345 mL). The reaction mixture was heated to 80° C. for 70 min, then was removed from heat an concentrated to ˜¼ volume by rotary evaporation. 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-(1-ethyl-5-oxo-2,5-dihydro-1H-pyrazol-3-yl)benzonitrile as a light-yellow solid (18.1 g) of sufficient purity to use in the next step without further purification. Calcd (M+1)+: 214.1. Found: 214.1.

Workup

customwas removed
temperaturefrom heat
concentrationan concentrated
customby rotary evaporation
customThe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with saturated aqueous sodium chloride solution
dry with materialthe washed solution was dried over sodium sulfate
filtrationThe dried solution was filtered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-28619cae3ae042aa8bae253f32b8497b
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871796B2

Reaction notes

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