4'-Fluoroacetophenone → HCID 9583323, compound

HRID 526743Notes

Reaction equation

HRID 526743 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.Cl.[NH:12]([C:14]([NH2:16])=[O:15])[NH2:13].C([O-])(=O)C.[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:13]/[NH:12][C:14]([NH2:16])=[O:15])/[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 11236Semicarbazide hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 9583323HCID 9583323, compoundYield 108%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(4-fluorophenyl)ethan-1-one (27.6 g, 199.80 mmol, 1.00 equiv) and hydrazinecarboxamide hydrochloride (22 g, 197.25 mmol, 0.99 equiv) in methanol (200 mL) was added a solution of sodium acetate (16.8 g, 204.79 mmol, 1.02 equiv) in water (80 mL) dropwise with stirring. The resulting solution was stirred at room temperature for 2 h. The solid was collected by filtration then air-dried to give 41.6 g of crude (E)-2-(1-(4-fluorophenyl)ethylidene)hydrazinecarboxamide as a white solid. LCMS (method A, ESI): RT=1.22 min, m/z=196.0 [M+H]+.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 2 h
  2. filtrationThe solid was collected by filtration
  3. customthen air-dried

Sources & evidence

ORD record
ord-0133a40307194f7e96d4b00be0623549
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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