Hydrazine, dihydrochloride → HCID 178467667, compound

HRID 872123Notes

Reaction equation

HRID 872123 reaction equation
[CH2:1]([O:3][CH2:4][C:5](=O)[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:7]#[N:8])[CH3:2].Cl.Cl.[NH2:19][NH2:20]>C(O)C>[CH2:1]([O:3][CH2:4][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[C:7]([NH2:8])[NH:20][N:19]=1)[CH3:2]

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 66635753HCID 66635753, compound

Product 1

HCID 178467667HCID 178467667, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Ethoxy-2-(4-methylphenyl)-3-oxobutanenitrile (1.493 g) is dissolved in ethanol (50 mL). After adding hydrazine 2HCl (1.10 g), TEA (0.85 mL) and molecular sieve, the reaction mixture is heated to 80° C. After stirring for 15 hours and cooling to room temperature, the molecular sieve is removed by filtering. The reaction solvent 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 to obtain the target compound (90%). 1H NMR (CDCl3, 300 MHz): δ 7.26 (m, 2H), 7.02 (m, 2H), 6.80 (br, 2H), 4.20 (s, 2H), 3.38 (m, 2H), 2.24 (s, 3H), 1.06 (t, 3H).

Workup

  1. temperaturecooling to room temperature
  2. customthe molecular sieve is removed
  3. filtrationby filtering
  4. customThe reaction solvent is removed under reduced pressure
  5. customAfter the reaction is terminated
  6. additionby adding saturated aq. NaHCO3
  7. extractionthe reaction mixture is extracted 3 times with ethyl acetate
  8. washThe organic layer is washed with water
  9. concentrationAfter concentration under reduced pressure
  10. customthe produced solid is recrystallized

Sources & evidence

ORD record
ord-7c65f689581e428da4ad2323a74d0556
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

Loading…