Diazomethane → Methyl 2-chloronicotinate

HRID 1870274Notes

Reaction equation

HRID 1870274 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:13])=[N-]>C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 762582-Chloronicotinic acid

Product 1

HCID 819931Methyl 2-chloronicotinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-chloronicotinic acid (15.75 g) in ethyl acetate (200 ml) was added excess diazomethane (ether solution) with stirring at room temperature. The reaction mixture was stirred at the same temperature for 30 minutes. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate with addition of charcoal. The title compound (15.5 g) was obtained by filtering the mixture and then evaporating under reduced pressure.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 30 minutes
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate with addition of charcoal

Sources & evidence

ORD record
ord-dacf109ff65049ae892278b929b8b730
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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