Methanol → HCID 12069505, compound

HRID 430218Notes

Reaction equation

HRID 430218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](N)=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][OH:16]>>[CH3:15][O:16][C:9](=[O:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 5216164-Chloro-3-nitrophenylacetamide

Product 1

HCID 12069505HCID 12069505, compoundYield 89%

Conditions

Temperature
25 °C

Procedure

A solution of 4-chloro-3-nitrophenylacetamide (2.00 g, 9.32 mmol) in methanol (40 mL) was treated with Amberlyst® 15 ion exchange resin (15.00 g). The resulting reaction mixture was heated under reflux for 64 h. The reaction mixture was allowed to cool to 25° C. and then filtered to remove the Amberlyst® 15 ion exchange resin. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded 4-chloro-3-nitrophenylacetic acid methyl ester (1.91 g, 89%) as a yellow oil: EI-HRMS m/e calcd for C9H8ClNO4 (M+) 229.0142, found 229.0146.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 64 h
  4. filtrationfiltered
  5. customto remove the Amberlyst® 15 ion exchange resin
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-20d0c287e55d4986bfd1232ce2610cc3
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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