4-Chloroaniline → ethyl acetoacetate, sodium salt

HRID 480068

Reaction equation

HRID 480068 reaction equation
ClC1C=CC(N)=CC=1.C([CH:11]([C:17]([CH3:19])=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])C.Cl.C([OH:23])C>>[O:23]=[C:11]([CH2:17][CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 3

HCID 78124-ChloroanilineHCID 79065Butanoic acid, 2-ethyl-3-oxo-, ethyl esterHCID 21887872Ethanol hydrochloride

Product 1

HCID 85195ethyl acetoacetate, sodium salt

Procedure

The p-chlorophenylhydrazone of ethyl 2-oxobutanoate was prepared by adaptation of the Japp-Klingemann reaction as described by Lions and Hughes (J. Proc. Roy. Soc. N.S. Wales 1939, 71: 445) to p-chloroaniline and ethyl 2-ethylacetoacetate. This phenylhydrazone was treated with HCl-ethanol according to the procedure of Lions and Hughes (J. Proc. Roy. Soc. N.S. Wales 1939, 71: 445) as applied therein to the corresponding bromophenylhydrazone. The title substance was collected by filtration as an orange solid after suspending the concentrated residue in water.

Workup

  1. filtrationThe title substance was collected by filtration as an orange solid

Sources & evidence

ORD record
ord-5293d7755e5f4c0ca75af02f1701131b
Source dataset
uspto-grants-2003_11
Patent number
US06649634B2

Linked notes

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