Hydrochloric Acid → 4-cyano-5-formyl-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazole

HRID 1655174Notes

Reaction equation

HRID 1655174 reaction equation
CN(C)C1C=CC([N+]([O-])=[CH:10][C:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=3)[N:14]=[CH:13][C:12]=2[C:27]#[N:28])=CC=1.Cl.C(OCC)(=[O:34])C>>[C:27]([C:12]1[CH:13]=[N:14][N:15]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=2)[C:11]=1[CH:10]=[O:34])#[N:28]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 88465577HCID 88465577, compound

Product 1

HCID 190203354-cyano-5-formyl-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazole

Procedure

To a stirred suspension of 7.6 grams (0.02 mole) of N-[4-(dimethylamino)phenyl]-a-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]nitrone in 300 mL of ethyl acetate was added 400 mL of aqueous 6N hydrochloric acid, at which time all of the solid material dissolved. The aqueous layer was separated and extracted with one portion of ethyl acetate. An aqueous solution saturated with sodium chloride was added to the aqueous layer, and the mixture was extracted several more times with ethyl acetate. The ethyl acetate extracts were combined with the organic layer, and the combination was washed with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was cooled and triturated with heptane, yielding 2.5 grams of 4-cyano-5-formyl-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazole. The nmr spectrum was consistent with the proposed structure. (The compounds of Steps E, F, and G were prepared by the method of E. C. Taylor et al., J. Org. Chem., 43, 4, 736 (1978).)

Workup

  1. dissolutionat which time all of the solid material dissolved
  2. customThe aqueous layer was separated
  3. extractionextracted with one portion of ethyl acetate
  4. additionAn aqueous solution saturated with sodium chloride was added to the aqueous layer
  5. extractionthe mixture was extracted several more times with ethyl acetate
  6. washthe combination was washed with water
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  10. temperatureThe oil was cooled
  11. customtriturated with heptane

Sources & evidence

ORD record
ord-e3bd070f7177471aa3df7aef857514ae
Source dataset
uspto-grants-1993_10
Patent number
US05250504

Reaction notes

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