Ethyl 2-acetyl-3-(dimethylamino)acrylate → HCID 71255694, compound

HRID 1508327Notes

Reaction equation

HRID 1508327 reaction equation
[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CN(C=C(C(=O)C)C(OCC)=O)C.Cl.ClC1C(F)=C(NN)C=CC=1>CCO>[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateHCID 25067375(3-Chloro-2-fluorophenyl)hydrazine--hydrogen chloride (1/1)HCID 71255694HCID 71255694, compound

Product 2

HCID 71255447HCID 71255447, compoundHCID 71255694HCID 71255694, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(3-chloro-2-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylate: (Reference: Herold, P. et al., Tetrahedron, 56:6497-6499 (2000)) A solution of ethyl 2-((dimethylamino)methylene)-3-oxobutanoate (0.517 g, 2.79 mmol), (3-chloro-2-fluorophenyl)hydrazine hydrochloride (0.500 g, 2.54 mmol) in EtOH (2.54 mL) and TEA (0.707 mL, 5.08 mmol) was stirred at rt. After 10 min, the reaction mixture was concentrated and purified by silica gel chromatography. The desired product, ethyl 1-(3-chloro-2-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylate (200 mg, 28%), was obtained as an off white solid. MS(ESI) m/z: 283.1 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-dad4ca497b434f2180587a43665204df
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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