4-Chloroaniline → ethyl acetoacetate, sodium salt

HRID 1760942Notes

Reaction equation

HRID 1760942 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-5812bb063e4745929799514b1b88c2b0
Source dataset
uspto-grants-2005_01
Patent number
US06846820B2

Reaction notes

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