Methylhydrazine → HCID 71087904, compound

HRID 1520772Notes

Reaction equation

HRID 1520772 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)/[CH:10]=[C:11](\O)/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1)#[N:2].[CH3:19][NH:20][NH2:21]>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:20]([CH3:19])[N:21]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 178473086HCID 178473086, compound

Product 1

HCID 71087904HCID 71087904, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon atmosphere (Z)-ethyl 4-(4-cyanophenyl)-2-hydroxy-4-oxobut-2-enoate (500 mg, 2.04 mmol, Eq: 1.00) was dissolved in Ethanol (10 ml) at rt. Methylhydrazine (95.9 mg, 110 μl, 2.04 mmol, Eq: 1.00) was added dropwise (The solution became yellow). The solution was stirred overnight at rt followed by 6 h heating at 50° C., cooled down to rt and concentrated. in vacuo. The residue was directly purified by column chromatography (20 g) Heptane/EtOAC:9/1 to give the expected pyrazole (173 mg, 33.2%) as a white solid. MS (ISP): 256.3 ([M+H]+).

Workup

  1. waitfollowed by 6 h
  2. temperatureheating at 50° C.
  3. temperaturecooled down to rt
  4. concentrationconcentrated
  5. customThe residue was directly purified by column chromatography (20 g) Heptane/EtOAC

Sources & evidence

ORD record
ord-46cbf8dd5c8c4c099cf0498efbe5e3a9
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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