Hydrochloric Acid → HCID 86692473, compound

HRID 1748556Notes

Reaction equation

HRID 1748556 reaction equation
[F:1][C:2]1[C:3]([NH:12][NH2:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CCOC=[CH:18][C:19](=O)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl.O.[CH2:29](O)C>>[CH2:24]([O:23][C:21]([C:20]1[CH:29]=[N:13][N:12]([C:3]2[C:2]([F:1])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][N:4]=2)[C:19]=1[CH3:18])=[O:22])[CH3:25]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 54463595Ethyl ethoxymethyleneacetoacetateHCID 552813773-Fluoro-2-hydrazinyl-5-(trifluoromethyl)pyridine

Product 1

HCID 86692473HCID 86692473, compound

Procedure

To a solution of 3-fluoro-5-(trifluoromethyl)pyridin-2-ylhydrazine in ethanol (166 ml) were added ethyl (2-ethoxymethylene)acetoacetate (4.52 g) synthesized according to the method described in J. Chem. Soc. Perkin trans. I, p. 1875 (1988) and 1 N hydrochloric acid aqueous solution (110 ml), and stirred under reflux for 3 hours. After the mixture was allowed to cool, to the reaction solution was added water, the precipitated solid was collected by filtration, washed with water, and then dried at 60° C. under air blow to give 1-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (5.16 g) as a white solid. MS (ESI) m/z: 318 (M+H)+.

Workup

  1. customsynthesized
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool, to the reaction solution
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried at 60° C. under air blow

Sources & evidence

ORD record
ord-f9c3b3b180d244c6acc25edc7c088589
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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