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

HRID 513644Notes

Reaction equation

HRID 513644 reaction equation
CN(C)/C=[CH:4]/[C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1.C1C[O:22]CC1.O>>[N+:15]([C:14]1[C:5]([CH:4]=[O:22])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 10586304(E)-N,N-dimethyl-2-(8-nitroquinolin-7-yl)ethenamine2×HCID 21881883Oxolane--water (1/1)

Product 1

HCID 117695548-Nitro-7-quinolinecarboxaldehydeYield 71%

Procedure

NalO4 (11.71 g, 54.76 mmol) was added portionwise to a solution of dimethyl-[(E)-2-(8-nitro-quinolin-7-yl)-vinyl]-amine (Intermediate 203) (4.44 g, 18.3 mmol) in THF/water (1:1, 70 ml). The mixture was stirred at room temperature for 16 h. The insoluble material was removed by filtration and washed with EtOAc (60 ml). The combined organic phases were washed with sat. sodium bicarbonate solution, brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (3.24 g, 71%).

Workup

  1. customThe insoluble material was removed by filtration
  2. washwashed with EtOAc (60 ml)
  3. washThe combined organic phases were washed with sat. sodium bicarbonate solution, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c54549d621aa4308be8cf37efda606b3
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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