Hydrazine → 2-(4-Fluorophenyl)acetohydrazide

HRID 390332Notes

Reaction equation

HRID 390332 reaction equation
[NH2:1][NH2:2].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](Cl)=[O:12])=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:1][NH2:2])=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 37449884-Fluorophenylacetyl chloride

Product 1

HCID 37716122-(4-Fluorophenyl)acetohydrazideYield 125.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of hydrazine (0.46 mL, 14.49 mmol, 2.5 equiv) in CH2Cl2 (29 mL) was added slowly over 30 sec 2-(4-fluorophenyl)acetyl chloride (0.79 mL, 5.79 mmol, 1.0 equiv). Slight warming of the mixture and white precipitate were observed. After stirring 45 min, the mixture was poured into a saturated aqueous solution of NaHCO3, layered with CH2Cl2 forming a thick emulsion. This emulsion was filtered through a medium glass frit to give a biphasic homogenous solution. This was extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo to provide the title compound (1.22 g, 124% yield) as a white solid. Source of extra mass is unclear as product is of high purity. Extra mass may reflect a measuring error of the acid chloride. 1H NMR (400 MHz, CDCl3) δ ppm 7.19-7.24 (m, 2H), 6.99-7.07 (m, 2H), 6.60 (s, 1H), 3.85 (d, J=2.01 Hz, 2H), 3.52 (s, 2H); LCMS (ES+, (M+H)+) m/z 169.22.

Workup

  1. temperatureSlight warming of the mixture and white precipitate
  2. filtrationThis emulsion was filtered through a medium glass frit
  3. customto give a biphasic homogenous solution
  4. extractionThis was extracted with CH2Cl2 (×3)
  5. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1afdcd9b449437f87f5442ff16a323f
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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