Pyridine → Ethyl-3-Chloromethyl-4-oxo-3-H-phthalazin-1-ylacetate

HRID 1199502Notes

Reaction equation

HRID 1199502 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17]O)[N:7]=1)[CH3:2].CS([Cl:24])(=O)=O.N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17][Cl:24])[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 14519538HCID 14519538, compound

Product 1

HCID 14519542Ethyl-3-Chloromethyl-4-oxo-3-H-phthalazin-1-ylacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl-3-hydroxymethyl-4-oxo-3-H-phthalazin-1-ylacetate (1.31 g) and methanesulfonyl chloride (0.69 g) in methylene chloride (10 ml) containing pyridine (0.8 ml) was stirred at room temperature overnight. Upon evaporation of methylene chloride and purification of the residue by chromatography on silica gel, eluting with a mixture of a chloroform and ethyl acetate (9:1), the title product was obtained (yield: 0.51 g; m.p. 99°-100° C.).

Workup

  1. customUpon evaporation of methylene chloride and purification of the residue by chromatography on silica gel
  2. washeluting with a mixture of a chloroform and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-a0308490186840cc9a2f7a39fbe150d3
Source dataset
uspto-grants-1990_02
Patent number
US04900844

Reaction notes

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