Hydrazine → HCID 178489088, compound

HRID 624342Notes

Reaction equation

HRID 624342 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10](=O)[CH3:11].[NH2:13][NH2:14].C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]2[C:3]=1[C:10]([CH3:11])=[N:13][NH:14]2

Participants

5

Reactant 3

HCID 9321HydrazineHCID 517045Sodium AcetateHCID 27373552'-Fluoro-6'-methoxyacetophenone

Product 1

HCID 178489088HCID 178489088, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

A solution of 1-(2-fluoro-6-methoxyphenyl)ethanone (1 g), hydrazine (1.04 g), and sodium acetate (0.49 g) was stirred for 72 hours in toluene (10 mL). The mixture was concentrated, taken up in DMSO (8 mL), and heated to 135° C. for 24 hours. The mixture was cooled, poured into ethyl acetate (200 mL), and rinsed with 3× water, and brine. The organic layer was concentrated and chromatographed on silica gel using 10-100% ethyl acetate/hexanes.

Workup

  1. concentrationThe mixture was concentrated
  2. temperatureThe mixture was cooled
  3. additionpoured into ethyl acetate (200 mL)
  4. washrinsed with 3× water, and brine
  5. concentrationThe organic layer was concentrated
  6. customchromatographed on silica gel using 10-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-49a5736581524171a16b0e60453824dd
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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