Acetoacetanilide → HCID 178418293, compound

HRID 2850

Reaction equation

HRID 2850 reaction equation
[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[OH-].[Na+].[Cl-].[C:17]1([N+:23]#[N:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[C:8]1([NH:7][C:1](=[O:6])[C:2](=[N:24][NH:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:3](=[O:4])[CH3:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7592AcetoacetanilideHCID 14798Sodium HydroxideHCID 60992Benzenediazonium chloride

Product 1

HCID 178418293HCID 178418293, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.5 g (25.4 mmol) of acetoacetanilide, a solution of 3.46 g (89 mmol) of NaOH in 45 ml of water and 95 mmol of phenyldiazonium chloride were treated as described in preparation 8. The residue was crystallised from EtOH, yielding 3.4 g of the title compound. M.p.=96°-97° C.

Workup

  1. customas described in preparation 8
  2. customThe residue was crystallised from EtOH

Sources & evidence

ORD record
ord-f388a24479e44c98bc290884466e1ad3
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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