Water → 2-[(5-Chloro-2-fluoro-phenyl)-hydrazono]-propionic acid ethyl ester

HRID 853063Notes

Reaction equation

HRID 853063 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([NH:8][NH2:9])[CH:7]=1.[C:11]([O:16][CH2:17][CH3:18])(=[O:15])[C:12]([CH3:14])=O.O>ClCCl>[CH2:17]([O:16][C:11](=[O:15])[C:12](=[N:9][NH:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[F:10])[CH3:14])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 12041Ethyl pyruvateHCID 2773732(5-chloro-2-fluorophenyl)hydrazine

Product 1

HCID 865847132-[(5-Chloro-2-fluoro-phenyl)-hydrazono]-propionic acid ethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(5-Chloro-2-fluoro-phenyl)-hydrazine (22.5 g, 140 mmol) was dissolved in dichloromethane (80 mL). Ethyl pyruvate (16.3 mL, 140 mmol) was added slowly to this solution at room temperature. The mixture was stirred for another1 h at room temperature, added to water and extraxcted with dichloromethane. Organic phases were pooled, washed subsequently with hydrochloric acid (1 N) and brine and dried with MgSO4. Solvents were removed in vacuo and the residue was triturated with n-hexane to yield the title product as beige solid (22.8 g, 62.9%), ISP-MS: m/e=259.1 (M+H+).

Workup

  1. washwashed subsequently with hydrochloric acid (1 N) and brine
  2. dry with materialdried with MgSO4
  3. customSolvents were removed in vacuo
  4. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-54d6c07da5d34cd88ddbc15d3d1b82c5
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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