Acetic Acid → HCID 178418695, compound

HRID 10234Notes

Reaction equation

HRID 10234 reaction equation
[C:1]([CH:3]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14])[C:4](=O)[CH3:5])#[N:2].O.[NH2:16][NH2:17].C(O)(=O)C>C1(C)C=CC=CC=1>[NH2:2][C:1]1[NH:17][N:16]=[C:4]([CH3:5])[C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 15486935HCID 15486935, compound

Product 1

HCID 178418695HCID 178418695, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-cyano-1-(2,4-dimethylphenyl)propan-2-one (43.8 g, 0.23 mol), hydrazine-hydrate (22 mL, 0.46 mol), glacial acetic acid (45 mL, 0.78 mol) and toluene (500 mL) were stirred at reflux temperature for 18 hours in an apparatus fitted with a Dean-Stark trap. The reaction mixture was cooled to ambient temperature and solvent was removed in vacuo. The residue was dissolved in 6N HCl and the resulting solution was extracted with ether three times. A concentrated ammonium hydroxide solution was added to the aqueous layer until pH=11. The resulting semi-solution was extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. Solvent was removed in vacuo to give a pale brown viscous oil (34.6 g, 75% yield): NMR (CDCl3,300 MHz): 7.10 (s, 1H), 7.05 (d, 2H, J=1), 2.37 (s, 3H), 2.10 (s, 3H); CI-MS: 202 (M+H).

Workup

  1. temperatureat reflux temperature for 18 hours in an apparatus
  2. customfitted with a Dean-Stark trap
  3. customsolvent was removed in vacuo
  4. dissolutionThe residue was dissolved in 6N HCl
  5. extractionthe resulting solution was extracted with ether three times
  6. additionA concentrated ammonium hydroxide solution was added to the aqueous layer until pH=11
  7. extractionThe resulting semi-solution was extracted three times with ethyl acetate
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. filtrationfiltered
  10. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-d1bb8a0a8ba549718554f7c939ed38d2
Source dataset
uspto-grants-2006_08
Patent number
US07094782B1

Reaction notes

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