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

HRID 1607984Notes

Reaction equation

HRID 1607984 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-473d07cc61bf4c73be2ba737923f8f2d
Source dataset
uspto-grants-1989_09
Patent number
US04868301

Reaction notes

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