Aniline → HCID 178468312, compound

HRID 564755Notes

Reaction equation

HRID 564755 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH3:17][C:18](=[O:23])[CH2:19][C:20](=[O:22])[CH3:21]>Cl.O.C(O)C>[C:2]1([NH:1][N:8]=[C:19]([C:18](=[O:23])[CH3:17])[C:20](=[O:22])[CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468312HCID 178468312, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Aniline (20 g, 0.215 mol) was dissolved in a mixture of concentrated hydrochloric acid (64 ml) and water (64 ml). To the resulting mixture was added dropwise at 0° C. a solution of sodium nitrite (16.3 g, 0.24 mol) in water (80 ml). The resulting diazonium salt was added to a mixture of sodium acetate (53 g, 0.64 mol), ethanol (225 ml) and pentane-2,4-dione (21.5 g, 0.22 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), 50% aqueous ethanol (2×50 ml), heptane (50 ml) and dried in vacuo at 50° C. for 18 h affording 39.3 g (90%) of 3-(phenylhydrazono)-pentane-2,4-dione as a solid.

Workup

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

Sources & evidence

ORD record
ord-843c450291084212b012fe0b6c1c0126
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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