Ethyl Acetoacetate → HCID 178429165, compound

HRID 1016449Notes

Reaction equation

HRID 1016449 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]1[C:13]([CH3:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[CH3:16].[C:17](OCC)(=[O:22])[CH2:18][C:19]([CH3:21])=O>C(O)(=O)C>[OH:22][C:17]1[N:6]2[N:5]=[C:4]([CH3:7])[C:3]([C:8]3[C:13]([CH3:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=3[CH3:16])=[C:2]2[N:1]=[C:19]([CH3:21])[CH:18]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178426114HCID 178426114, compound

Product 1

HCID 178429165HCID 178429165, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

Dissolve 5-amino-4-(4-chloro-2,6-dimethylphenyl)-3-methylpyrazole in 20 mL glacial acetic acid at ambient temperature, and add ethyl acetoacetate (2.0 mL, 1.99 g). Heat to reflux (130° C.) under N2 overnight. Evaporate down to concentrate and add 200 mL Et2O to precipitate out product. Stir at ambient temperature for 1 hour, then filter and wash the resulting white solid (1.25 g) with copious amounts of Et2O. LCMS=302.2 (MH+); 300.2 (M−).

Workup

  1. temperatureHeat
  2. customEvaporate down
  3. concentrationto concentrate
  4. additionadd 200 mL Et2O
  5. customto precipitate out product
  6. filtrationfilter
  7. washwash the resulting white solid (1.25 g) with copious amounts of Et2O

Sources & evidence

ORD record
ord-9a95ae0c6fa34d1f841cfbd82e94716b
Source dataset
uspto-grants-2002_11
Patent number
US06476038B1

Reaction notes

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