Cornforth reagent → N-(5-chloro-2-formylphenyl)formamide

HRID 350604Notes

Reaction equation

HRID 350604 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][OH:12])=[C:6]([NH:8][CH:9]=[O:10])[CH:7]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:11]=[O:12])=[C:6]([NH:8][CH:9]=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 12083233N-(5-chloro-2-hydoxymethylphenyl)formamide

Product 1

HCID 12083234N-(5-chloro-2-formylphenyl)formamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1.40 g of the product from stage 1 and 3.40 g of pyridinium dichromate in 350 ml of anhydrous dichloromethane was stirred for 24 hours at 20° C. The solution was then filtered and the filtrate was concentrated by evaporation in vacuo. The residue was purified by flash chromatography on silica gel with ethyl acetate/cyclohexane (1/1) as eluent, 0.88 g (64% of theory) of the title compound being obtained in crystalline form.

Workup

  1. filtrationThe solution was then filtered
  2. concentrationthe filtrate was concentrated by evaporation in vacuo
  3. customThe residue was purified by flash chromatography on silica gel with ethyl acetate/cyclohexane (1/1) as eluent

Sources & evidence

ORD record
ord-00418f60caba4a63b26a69588493ab5f
Source dataset
uspto-grants-2007_02
Patent number
US07183274B2

Reaction notes

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