Hydrochloric Acid → HCID 67493549, compound

HRID 1921251Notes

Reaction equation

HRID 1921251 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[CH2:11]([O:13][C:14]([C:16]#[C:17][C:18](OCC)=O)=[O:15])[CH3:12].C(=O)([O-])[O-].[K+].[K+].Cl>O.C(O)C>[CH2:11]([O:13][C:14]([C:16]1[CH:17]=[C:18]([Cl:1])[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[F:2])[N:10]=1)=[O:15])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69803Diethyl acetylenedicarboxylateHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)

Product 1

HCID 67493549HCID 67493549, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a flask were 2-fluorophenylhydrazine hydrochloride (12.2 g, 75 mmol), diethylacetylene dicarboxylate (12.8 g, 75 mmol), potassium carbonate (20.7 g, 150 mmol), and ethanol (200 ml) placed and the resulting slurry heated at reflux for 5 hours. The mixture was cooled to room temp, diluted with water (400 ml) and acidified carefully with 2M hydrochloric acid. The mixture was stirred for 2 h then the resulting suspended solid collected by filtration, washed with water (3×50 ml) and dried in vacuo giving 11.4 g of 5-Chloro-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester [U1]. 1H NMR (300 MHz., DMSO): δ 1.29 (3H,t), 4.25 (2H,q), 5.92 (1H,s), 7.34-7.60 84H,m), 11.90 (1H,s,br). LCMS (Method A): RT=1.75 min, (M+H)+=251.

Workup

  1. customIn a flask were
  2. temperaturethe resulting slurry heated
  3. temperatureat reflux for 5 hours
  4. filtrationcollected by filtration
  5. washwashed with water (3×50 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1801a89c078c4379af314827879059bf
Source dataset
uspto-grants-2012_05
Patent number
US08173680B2

Reaction notes

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