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

Potassium Carbonate → 2,5-Dichloropyridine-4-carbonitrile

HRID 637791
Notes
Print preview

Reaction equation

HRID 637791 reaction equation
O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[CH:12]=[C:11]([CH:13]=[N:14]O)[C:10]([Cl:16])=[CH:9][N:8]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]#[N:14])[C:10]([Cl:16])=[CH:9][N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 1363872824-Pyridinecarboxaldehyde, 2,5-dichloro-, oxime

Product 1

HCID 135602102,5-Dichloropyridine-4-carbonitrileYield 77.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 100 ml of acetonitrile was added 24.5 g of POCl3, followed by 27.1 g of 2,5-dichloro-4-pyridinecarboxaldehyde oxime (prepared as described in Example 4). The reaction mixture was heated at reflux temperature for 1 hour, then cooled and poured onto 300 g of ice. The pH of the mixture was adjusted to about pH 6 with K2CO3 and filtered. The filtrate was extracted with 100 ml of CH2Cl2. The filter cake and the CH2Cl2 solution were combined, diluted with equal volumes of hexane, treated with charcoal, dried, and concentrated. The residue was purified by distillation on a Kugelrohr distillation apparatus (boiling point 80° C. at 0.2 mm pressure) to give 19.0 g (77%) of the desired 2,5-dichloro-4-pyridinecarbonitrile as a white solid, m.p. 58°-60° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. extractionThe filtrate was extracted with 100 ml of CH2Cl2
  6. additiondiluted with equal volumes of hexane
  7. additiontreated with charcoal
  8. customdried
  9. concentrationconcentrated
  10. distillationThe residue was purified by distillation on a Kugelrohr distillation apparatus (boiling point 80° C. at 0.2 mm pressure)

Sources & evidence

ORD record
ord-ce726209030f425f86002d234f826cb2
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04558134

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes