6-Amino-5-chloropyridine-3-carbonyl chloride → 1-(6-Amino-5-chloropyridin-3-YL)ethan-1-one

HRID 330357Notes

Reaction equation

HRID 330357 reaction equation
[Cl:1][C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[C:12]([O-])(=O)CC([O-])=O.C(C(CC)(O[Mg+2])C)C>O1CCCC1>[NH2:11][C:3]1[C:2]([Cl:1])=[CH:10][C:6]([C:7](=[O:8])[CH3:12])=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 143713826-Amino-5-chloropyridine-3-carbonyl chloride

Product 1

HCID 143713831-(6-Amino-5-chloropyridin-3-YL)ethan-1-oneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7.2 g (37.5 mmol) of 5-chloro-6-aminonicotinoyl chloride in 10 ml of absolute tetrahydrofuran are added to a boiling solution of 8.55 g (37.5 mmol) of diethyl ethoxymagnesium-malonate (prepared in accordance with Org. Synth. Coll. Vol. IV (1963), 285) in 120 ml of absolute tetrahydrofuran and the mixture is heated under reflux for 2 hours. After neutralization with 2N sulphuric acid, the organic phase is separated off and evaporated. The residue is heated under reflux in a mixture of 30 ml of glacial acetic acid, 20 ml of water and 5 ml of concentrated sulphuric acid for 4 hours. The mixture is stirred into ice-water, brought to pH 4 and extracted with ethyl acetate. Drying and evaporation gives 5.4 g (85%) of the title compound, melting point: 188° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customAfter neutralization with 2N sulphuric acid, the organic phase is separated off
  4. customevaporated
  5. temperatureThe residue is heated
  6. temperatureunder reflux in a mixture of 30 ml of glacial acetic acid, 20 ml of water and 5 ml of concentrated sulphuric acid for 4 hours
  7. extractionextracted with ethyl acetate
  8. customDrying
  9. customevaporation

Sources & evidence

ORD record
ord-d587d398ed39445cb11f23e7d47288ca
Source dataset
uspto-grants-1990_01
Patent number
US04895950

Reaction notes

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