Ammonia → Methyl 2-amino-5-chloronicotinate

HRID 251842

Reaction equation

HRID 251842 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH3:13]>CC(C)=O.CO>[NH2:13][C:2]1[N:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2764318Methyl 2,5-Dichloronicotinate

Product 1

HCID 15828199Methyl 2-amino-5-chloronicotinateYield 148.1%

Reagents, catalysts & solvents 1

HCID 21894497Aceton-methanolSolvent

Procedure

Performed in duplicate on identical scales in two pressure vessels, methyl 2,5-dichloronicotinate (4.5 g, 22 mmol) was dissolved in ammonia solution (250 mL, 0.5 M in 1,4-dioxane; 0.125 mol). The pressure vessels were sealed and heated at (85±5)° C. for 9 days. The two reaction mixtures were allowed to cool to room temperature, then combined and concentrated under reduced pressure to yield a white solid. Dissolution of the solid in 1:1 acetone-MeOH (˜500 mL), followed by adsorption onto silica gel (25 g) and then purification by flash column chromatography (25:10:1 hexane-CH2Cl2-Et2O), gave 6.08 g (75%) of methyl 2-amino-5-chloronicotinate.

Workup

  1. customThe pressure vessels were sealed
  2. temperatureheated at (85±5)° C
  3. customThe two reaction mixtures
  4. concentrationconcentrated under reduced pressure
  5. customto yield a white solid
  6. custompurification by flash column chromatography (25:10:1 hexane-CH2Cl2-Et2O)

Sources & evidence

ORD record
ord-e814209b787b446abea0c0f4eaf7d7f4
Source dataset
uspto-grants-2011_01
Patent number
US07868006B2

Linked notes

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