Acetic Acid → HCID 178509102, compound

HRID 872119Notes

Reaction equation

HRID 872119 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]([CH:13]2[CH2:15][CH2:14]2)=O)[C:9]#[N:10])=[CH:4][CH:3]=1.O.[NH2:17][NH2:18].C(O)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:11]([CH:13]3[CH2:14][CH2:15]3)=[N:17][NH:18][C:9]=2[NH2:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 145579492-(4-Chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile

Product 1

HCID 178509102HCID 178509102, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(4-Chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile(7.74 g), hydrazine hydrate (3.5 mL) and acetic acid (7.5 mL) are dissolved in a toluene solvent and stirred for 16 hours while heating. Upon completion of reaction, after cooling to room temperature, the solvent is removed by distillation under reduced pressure. The remainder is extracted with water and ethyl acetate. The extracted organic layer is dehydrated and distilled under reduced pressure. The remainder is purified by column chromatography to yield 5.2 g of the target compound. 1H NMR (CDCl3, 300 MHz): δ 7.40 (m, 4H), 3.75 (br, 2H), 1.86 (m, 1H) 0.93 (m, 2H), 0.65 (m, 2H).

Workup

  1. temperaturewhile heating
  2. customUpon completion of reaction
  3. customthe solvent is removed by distillation under reduced pressure
  4. extractionThe remainder is extracted with water and ethyl acetate
  5. distillationdistilled under reduced pressure
  6. customThe remainder is purified by column chromatography

Sources & evidence

ORD record
ord-1c30b828453d453db34398dc65172c1c
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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