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Methyl iodide → 6-Chloro-4-methylamino-3-nitro-pyridine-2-carbonitrile

HRID 517935
Notes
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Reaction equation

HRID 517935 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12].[C:14](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.C(OCC)(=O)C>[CH3:14][NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 552704134-Amino-6-chloro-3-nitropicolinonitrile

Product 1

HCID 576575586-Chloro-4-methylamino-3-nitro-pyridine-2-carbonitrileYield 97.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 4-amino-6-chloro-3-nitro-pyridine-2-carbonitrile (12.5 g), potassium carbonate (17.4 g) and iodomethane (22.5 g) in acetonitrile (150 ml) was heated at 80° C. for 3 hours. At this point, another portion of iodomethane (22.5 g) was added; the mixture was heated with stirring for another 2 hours. The mixture was then diluted with ethyl acetate (500 ml) and washed with water (150 ml). The organic layer was then dried over sodium sulphate, solvent removed under reduced pressure to give expected product 4-methylamino-6-chloro-3-nitro-pyridine-2-carbonitrile (13 g).

Workup

  1. temperaturethe mixture was heated
  2. washwashed with water (150 ml)
  3. dry with materialThe organic layer was then dried over sodium sulphate, solvent
  4. customremoved under reduced pressure

Sources & evidence

ORD record
ord-22d7a36af1b0488f8e3345be00320352
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115126B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes