Water → (E)-N,N-dimethyl-2-(8-nitroquinolin-7-yl)ethenamine

HRID 513643Notes

Reaction equation

HRID 513643 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].O>CN(C=O)C>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 819817-Methyl-8-nitroquinoline

Product 1

HCID 10586304(E)-N,N-dimethyl-2-(8-nitroquinolin-7-yl)ethenamineYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-methyl-8-nitroquinoline (6 g, 31.9 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (4.27 ml, 31.9 mmol) in DMF (15 ml) was heated at 140° C., under nitrogen, for 16 h. After cooling to room temperature, water (15 ml) was added and the resulting precipitate was collected by filtration, washed with EtOAc and dried to give the title compound (4.4 g, 57%). The compound could not be detected by HPLCMS therefore structure was confirmed by 1H NMR.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with EtOAc
  3. customdried

Sources & evidence

ORD record
ord-a96435af3cb04ec796ca1e04eeae6d41
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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