HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2079524
Notes
Print preview

Reaction equation

HRID 2079524 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-a63f8ce408714fa2852b30ed9d6eb399
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932251B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes