Diethyl Ether → Ethyl 3-chloro-4-(2-pyridyl)-2,4-dioxo-butyrate hydrochloride

HRID 1905985Notes

Reaction equation

HRID 1905985 reaction equation
S(Cl)([Cl:4])(=O)=O.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:21])[CH2:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(OCC)C>C(Cl)Cl>[ClH:4].[Cl:4][CH:13]([C:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=1)=[O:21])[C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24648Sulfuryl chlorideHCID 12171345Ethyl 2,4-dioxo-4-(pyridin-2-yl)butanoate

Product 1

HCID 20144948Ethyl 3-chloro-4-(2-pyridyl)-2,4-dioxo-butyrate hydrochlorideYield 182.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of sulfuryl chloride (2.84 g) in methylene chloride (5 ml) was dropwise added to a solution of ethyl 4-(2-pyridyl)-2,4-dioxobutyrate (4.42 g) in methylene chloride (60 ml) at 8° C. to 25° C. After the mixture was stirred for 30 minutes at ambient temperature, diethyl ether (60 ml) was added thereto. The precipitated crystals were collected by filtration, washed with diethyl ether and dried to give ethyl 3-chloro-4-(2-pyridyl)-2,4-dioxo-butyrate hydrochloride (5.6 g).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-6f2e6a7921fc4c7e804fe81c1829cd00
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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