Hydrochloric Acid → 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-1H-pyrazole-4-carbaldehyde

HRID 2090876Notes

Reaction equation

HRID 2090876 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH:16]=[C:15]([C:17](OC)=[O:18])[C:14]([CH3:21])=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[C:3]([N:12]2[CH:16]=[C:15]([CH:17]=[O:18])[C:14]([CH3:21])=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 66778425methyl 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 433486331-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-1H-pyrazole-4-carbaldehydeYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (150 mL) of methyl 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methyl-1H-pyrazole-4-carboxylate (7.0 g) synthesized above in tetrahydrofuran was added dropwise diisobutylaluminum hydride (1.5M toluene solution, 58.4 mL) at 0° C. After stirring for 30 min, the reaction mixture was poured into 2N hydrochloric acid of 0° C., and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was evaporated. The residue was treated in the same manner as in Example 1(5) to give the title object compound (1.7 g, 27%) as a pale-yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f81df87bddb24227b013d54ddfa8437b
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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