4-Methoxyphenylhydrazine hydrochloride → HCID 13019919, compound

HRID 610139Notes

Reaction equation

HRID 610139 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1>C(O)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:9]([CH3:8])=[CH:4][C:5]([CH3:6])=[N:11]2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 13019919HCID 13019919, compoundYield 190.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-methoxyphenylhydrazine hydrochloride (118.7 g, 0.68 mol) in 300 mL of glacial acetic acid was added 2, 4-pentanedione (68.0 g, 0.68 mol). The resulting solution was stirred at 100° C. for 18 h and then was cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate, filtered through a pad of silica gel and concentrated to afford 131 g (95%) of the title compound, which was used without purification. LRMS (NH4 -CI): 203.3 (M+H)+.

Workup

  1. temperaturewas cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7a675407bb74af88657995b99df998d
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

Loading…