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

HRID 472042Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-9ab98d60404b45b0b6ec7b1590ec7f2a
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633193B2

Reaction notes

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