8-Nitro-7-quinolinecarboxaldehyde → (8-Nitro-quinolin-7-yl)-phenyl-methanol

HRID 513653Notes

Reaction equation

HRID 513653 reaction equation
[N+:1]([C:4]1[C:5]([CH:14]=[O:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].Br[Mg][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[N+:1]([C:4]1[C:5]([CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 117695548-Nitro-7-quinolinecarboxaldehyde2×HCID 178418255HCID 178418255, compound

Product 1

HCID 68183066(8-Nitro-quinolin-7-yl)-phenyl-methanolYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-nitro-quinoline-7-carbaldehyde (Intermediate 204) (1.14 g, 5.64 mmol) in dry THF (10 ml) was cooled to 0° C. in an ice bath. Bromo(phenyl)magnesium (1 M in THF; 5.64 ml) was added and the reaction mixture was stirred at room temperature for 30 min. The reaction was quenched with sat. ammonium chloride (10 ml) and the resulting organic phase was extracted with EtOAc (20 ml). The combined organic phases were washed with brine (10 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc (60:40) as the eluent, to give the title compound (1.09 g, 60%).

Workup

  1. customThe reaction was quenched with sat. ammonium chloride (10 ml)
  2. extractionthe resulting organic phase was extracted with EtOAc (20 ml)
  3. washThe combined organic phases were washed with brine (10 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with heptane/EtOAc (60:40) as the eluent

Sources & evidence

ORD record
ord-4547f73ad4f5438f8ebbafd05bfe14a7
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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