P-Anisidine → HCID 178492416, compound

HRID 564748Notes

Reaction equation

HRID 564748 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[N:10]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH3:19][C:20](=[O:25])[CH2:21][C:22](=[O:24])[CH3:23]>Cl.O.C(O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][N:10]=[C:21]([C:20](=[O:25])[CH3:19])[C:22](=[O:24])[CH3:23])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 7732P-AnisidineHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178492416HCID 178492416, compoundYield 60.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

4-Amino-anisole (15 g, 0.12 mol) was dissolved in a mixture of concentrated hydrochloric acid (36 ml) and water (36 ml). To the resulting mixture was added dropwise at 5° C. a solution of sodium nitrite (9.2 g, 0.13 mol) in water (45 ml). The resulting diazonium salt was added to a mixture of sodium acetate (30 g, 0.37 mol), ethanol (125 ml) and pentane-2,4-dione (12.2 g, 0.12 mol) at room temperature. The resulting mixture was stirred for 1 h at room temperature. The precipitate was filtered off and washed with water (2×150 ml), ethanol (2×50 ml) and dried in vacuo at 50° C. for 18 h affording 17 g (60%) of 3-[(4-methoxy-phenyl)-hydrazono]-pentane-2,4-dione as a solid.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water (2×150 ml), ethanol (2×50 ml)
  3. customdried in vacuo at 50° C. for 18 h

Sources & evidence

ORD record
ord-ee38d5e967bb4b94adf028c4fd2345c9
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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