Methanol → 4-[(2-methoxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one

HRID 362451Notes

Reaction equation

HRID 362451 reaction equation
[CH3:1][C:2]1[CH2:3][C:4](=[O:13])[N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH:14](OC)(OC)OC.[CH3:21][O:22][C:23]1[C:24]([NH2:29])=[CH:25][CH:26]=[CH:27][CH:28]=1.CO>C(O)(=O)C>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][CH:14]=[C:3]1[C:2]([CH3:1])=[N:6][N:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:4]1=[O:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 4021Mci-186HCID 70002-MethoxyanilineHCID 9005Trimethyl orthoformate

Product 1

HCID 1784895884-[(2-methoxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2 g of 5-methyl-2-phenyl-2,4-dihydro-3-pyrazolone, 188 ml of trimethyl orthoformate and 1.29 ml of o-anisidine are heated with stirring in 5 ml of glacial acetic acid at 70° C. for 2 h. The reaction mixture is cooled and 10 ml of methanol are added. The precipitate which has separated out is filtered off with suction and recrystallized from ethyl acetate.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe precipitate which has separated out
  3. filtrationis filtered off with suction
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a5a8ea6e2454456faa5d8fdb3e022197
Source dataset
uspto-grants-1999_02
Patent number
US05869516

Reaction notes

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