Acetic Acid → HCID 178426114, compound

HRID 842010Notes

Reaction equation

HRID 842010 reaction equation
[NH2:1][NH2:2].C(O)(=O)C.[Cl:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH:15]([C:18](=O)[CH3:19])[C:16]#[N:17])=[C:10]([CH3:21])[CH:9]=1>C1(C)C=CC=CC=1>[NH2:17][C:16]1[NH:2][N:1]=[C:18]([CH3:19])[C:15]=1[C:11]1[C:12]([CH3:14])=[CH:13][C:8]([Cl:7])=[CH:9][C:10]=1[CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 184069852-(4-Chloro-2,6-dimethylphenyl)-3-oxobutanenitrile

Product 1

HCID 178426114HCID 178426114, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
130 °C

Procedure

Dissolve anhydrous hydrazine (0.91 g, 0.90 mL) in 20 mL toluene. Add glacial acetic acid (2.25 mL) and allow to stand at ambient temperature for 10 minutes until solution becomes cloudy white. Add a solution of 2-(4-chloro-2,6-dimethylphenyl)-3-oxobutanenitrile in 10 mL toluene, rinsing out the ketonitrile flask with an additional 5 mL toluene. Heat to reflux under N2 (130° C.) with Dean-Stark trap attached. Water will begin to accumulate after 10 minutes or so. After 2 hours, evaporate down and partition between 1.0 N NaOH (100 mL) and EtOAc (100 mL). Extract aqueous layer with EtOAc (2×100 mL), then pool the organic layers and dry over Na2SO4. Filter and evaporate to yellow oil (1.75 g). Use without further purification. LCMS=236.5 (M+); 234.5 (M−)

Workup

  1. washrinsing out the ketonitrile flask with an additional 5 mL toluene
  2. temperatureHeat
  3. waitto accumulate after 10 minutes
  4. waitAfter 2 hours
  5. customevaporate down
  6. custompartition between 1.0 N NaOH (100 mL) and EtOAc (100 mL)
  7. dry with materialdry over Na2SO4
  8. filtrationFilter
  9. customevaporate to yellow oil (1.75 g)
  10. customUse without further purification

Sources & evidence

ORD record
ord-bc1386cb06324279b87e0c989f5f3918
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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