Acetic Acid → HCID 178494728, compound

HRID 872128Notes

Reaction equation

HRID 872128 reaction equation
[CH2:1]([O:3][CH2:4][C:5](=O)[CH:6]([C:9]1[CH:14]=[CH:13][C:12](C)=[CH:11][CH:10]=1)[C:7]#[N:8])C.O.[NH2:18][NH2:19].[C:20]([OH:23])(=O)C>C(O)C>[CH3:1][O:3][CH2:4][C:5]1[C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:23][CH3:20])=[CH:13][CH:14]=2)=[C:7]([NH2:8])[NH:19][N:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 66635753HCID 66635753, compound

Product 1

HCID 178494728HCID 178494728, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

4-Ethoxy-2-(4-methylphenyl)-3-oxobutanenitrile (1.493 g) is dissolved in ethanol (150 mL) and hydrazine hydrate (˜40%, 7.8 mL, 2 eq) and acetic acid (5.9 mL, 2 eq) are slowly added. The reaction mixture is stirred at 80° C.90° C. for 1 hour under reflux. Upon completion of the reaction, ethanol is removed under reduced pressure. After the reaction is terminated by adding saturated aq. NaHCO3, the reaction mixture is extracted 3 times with ethyl acetate. The organic layer is washed with water and dehydrated with MgSO4. After concentration under reduced pressure, the produced solid is recrystallized with Hx:EA:MC=20:1:0.1 to obtain the target compound (90%). 1H NMR (CDCl3, 300 MHz): δ 7.25 (m, 2H), 6.95 (m, 2H), 4.43 (s, 3H), 3.82 (s, 3H), 3.38 (s, 3H).

Workup

  1. temperature90° C. for 1 hour under reflux
  2. customis removed under reduced pressure
  3. customAfter the reaction is terminated
  4. additionby adding saturated aq. NaHCO3
  5. extractionthe reaction mixture is extracted 3 times with ethyl acetate
  6. washThe organic layer is washed with water
  7. concentrationAfter concentration under reduced pressure
  8. customthe produced solid is recrystallized with Hx

Sources & evidence

ORD record
ord-a2509d31fffe490d96f82d7fb2954413
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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