Hydrazine → 2-(4-Fluorophenyl)acetohydrazide

HRID 1822891Notes

Reaction equation

HRID 1822891 reaction equation
[NH2:1][NH2:2].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1>CO>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]([NH:1][NH2:2])=[O:4])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 2733233Methyl 2-(4-fluorophenyl)acetate

Product 1

HCID 37716122-(4-Fluorophenyl)acetohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Neat anhydrous hydrazine 20 mL was added to a slurry of (4-fluorophenyl)acetic acid methyl ester (Acros Organics USA, Morris Plains, N.J., 25.66 g, 152.5 mmol) in MeOH (120 mL) and the mixture was heated to 60° C. with reflux condenser under nitrogen for 2 hrs. Cooled to room temperature, evaporated to dryness (room temperature to 60° C., 100 Torr to 7 Torr). The solid residue was re-crystallized from 1-propanol , 100 mL (reflux to room temperature, overnight). The crystallized product was collected by filtration, washed with 1-propanol and dried on high vacuum. [1st fraction]

Workup

  1. temperaturewith reflux condenser under nitrogen for 2 hrs
  2. temperatureCooled to room temperature
  3. customevaporated to dryness (room temperature to 60° C., 100 Torr to 7 Torr)
  4. customThe solid residue was re-crystallized from 1-propanol , 100 mL (reflux to room temperature, overnight)
  5. filtrationThe crystallized product was collected by filtration
  6. washwashed with 1-propanol
  7. customdried on high vacuum

Sources & evidence

ORD record
ord-57bc1c7a73ab497db2a4d66d43c0e314
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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