Malonic Acid → HCID 67855009, compound

HRID 1655175Notes

Reaction equation

HRID 1655175 reaction equation
[C:1]([C:3]1[CH2:4][N:5]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][N:11]=2)[NH:6][C:7]=1[CH:8]=O)#[N:2].C(O)(=O)[CH2:22][C:23]([OH:25])=[O:24]>N1CCCCC1.N1C=CC=CC=1>[C:1]([C:3]1[CH2:4][N:5]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][N:11]=2)[NH:6][C:7]=1[CH:8]=[CH:22][C:23]([OH:25])=[O:24])#[N:2]

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 86746664HCID 86746664, compound

Product 1

HCID 67855009HCID 67855009, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Procedure

A stirred solution of 0.3 gram (0.001 mole) of 4-cyano-5-formyl-2-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazole, 0.2 gram (0.002 mole) of malonic acid, two drops of piperidine, and 3 mL of pyridine was heated at reflux for about 18 hours. After this time, the reaction mixture was cooled and was concentrated under reduced pressure to a residue. The residue was stirred with excess aqueous 2N hydrochloric acid and ethyl acetate. The organic layer was separated and washed with aqueous 2N hydrochloric acid and then with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was triturated several times with petroleum ether, and each time the supernatent liquid was discarded. The resultant solid was dried, yielding 3-[4-cyano-2-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylic acid. The nmr spectrum was consistent with the proposed structure and was identical to the nmr spectrum of this compound prepared by the method of Example 4.

Workup

  1. temperatureat reflux for about 18 hours
  2. temperatureAfter this time, the reaction mixture was cooled
  3. concentrationwas concentrated under reduced pressure to a residue
  4. customThe organic layer was separated
  5. washwashed with aqueous 2N hydrochloric acid
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residue
  9. customThe residue was triturated several times with petroleum ether
  10. customThe resultant solid was dried

Sources & evidence

ORD record
ord-bc1ac8a75d2749bc8664cd0dc0c8c8f3
Source dataset
uspto-grants-1993_10
Patent number
US05250504

Reaction notes

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