{(E)-2-[2-(2,6-dimethyl-phenyl)-5-nitro-pyridin-4-yl]vinyl}-dimethyl-amine → 5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

HRID 602546Notes

Reaction equation

HRID 602546 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](/[CH:15]=[CH:16]/N(C)C)[C:12]([N+:20]([O-])=O)=[CH:11][N:10]=1>C(O)(=O)C.[Zn]>[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]2[CH:15]=[CH:16][NH:20][C:12]2=[CH:11][N:10]=1

Participants

4

Reactant 1

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

Product 1

HCID 671524405-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of {(E)-2-[2-(2,6-dimethyl-phenyl)-5-nitro-pyridin-4-yl]-vinyl}-dimethyl-amine (10 g, 33.6 mmol) in glacial acetic acid (150 mL), zinc dust (22 g, 336 mmol) is added and the mixture is stirred at room temperature for 1 h. Temperature is raised to 90° C. at which the mixture is maintained for another 30 min. The resultant suspension is filtered over celite and concentrated under reduced pressure to afford 5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine as a brown solid.

Workup

  1. temperatureTemperature is raised to 90° C. at which the mixture
  2. temperatureis maintained for another 30 min
  3. filtrationThe resultant suspension is filtered over celite and
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a712d2c2d53f4c469af024d77e2dc7cb
Source dataset
uspto-grants-2011_03
Patent number
US07906528B2

Reaction notes

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