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Ammonium Chloride → 1-(2,6-Dichloropyridin-4-YL)ethanone

HRID 2043414
Notes
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Reaction equation

HRID 2043414 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:14])[N:13]=1)[C:5](N(OC)C)=[O:6].O1CCC[CH2:16]1.C[Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH3:16])[CH:11]=[C:12]([Cl:14])[N:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 219482182,6-Dichloro-N-methoxy-N-methylisonicotinamideHCID 178420675HCID 178420675, compound

Product 1

HCID 221194461-(2,6-Dichloropyridin-4-YL)ethanone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

490 mg of 2,6-dichloro-N-methoxy-N-methyl isonicotinamide was dissolved in tetrahydrofuran, 2.1 ml of 3M methyl magnesium bromide tetrahydrofuran solution was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 hour. To the reaction solution was added ammonium chloride aqueous solution, and the mixture was diluted with ethyl acetate. The mixture was washed with brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 325 mg of the objective compound.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-be0deae52f7643fcb73b1d27650ea9e1
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08586591B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes