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

tert-Butoxy bis(dimethylamino)methane → {(E)-2-[2-(2,6-dimethyl-phenyl)-5-nitro-pyridin-4-yl]vinyl}-dimethyl-amine

HRID 602545
Notes
Print preview

Reaction equation

HRID 602545 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=1.CC(O[CH:24](N(C)C)[N:25]([CH3:27])[CH3:26])(C)C>CN(C=O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:14]=[C:13](/[CH:15]=[CH:24]/[N:25]([CH3:27])[CH3:26])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 671525442-(2,6-Dimethyl-phenyl)4-methyl-5-nitro-pyridine

Product 1

HCID 86624080{(E)-2-[2-(2,6-dimethyl-phenyl)-5-nitro-pyridin-4-yl]vinyl}-dimethyl-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the 2-(2,6-dimethyl-phenyl)4-methyl-5-nitro-pyridine (8 g, 33.0 mmol) in anhydrous DMF (30 mL), Bredereck's reagent (20 mL, 99.0 mmol) is added, and the mixture is heated for 1 h at 90° C. The mixture is concentrated under reduced pressure, and the residue is dissolved a mixture of EtOAc-hexane-DCM (1:1:1, 200 mL) and filtered over small pad of silica gel. Removal of the solvent under reduced pressure gives the crude {(E)-2-[2-(2,6-dimethyl-phenyl)-5-nitro-pyridin-4-yl]-vinyl}-dimethyl-amine which is used in the following step.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved
  3. additiona mixture of EtOAc-hexane-DCM (1:1:1, 200 mL)
  4. filtrationfiltered over small pad of silica gel
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0cbc7fe2ad6b4d8d9ae979503c6138e1
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906528B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes