8-Nitro-7-quinolinecarboxaldehyde → (3-Fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanol

HRID 513658Notes

Reaction equation

HRID 513658 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[N+:10]([C:13]1[C:14]([CH:23]=[O:24])=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2)([O-:12])=[O:11]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:23]([C:14]2[C:13]([N+:10]([O-:12])=[O:11])=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[N:21]3)=[CH:16][CH:15]=2)[OH:24])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 117695548-Nitro-7-quinolinecarboxaldehyde2×HCID 178505773HCID 178505773, compound

Product 1

HCID 68183441(3-Fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanolYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Fluorophenyl magnesium bromide (1 M solution in THF; 0.86 ml, 4.33 mmol) was added dropwise to a solution of 8-nitroquinoline-7-carbaldehyde (Intermediate 204) (0.35 g, 1.73 mmol) in dry THF (5 ml) at −78° C. and the mixture was stirred at −78° C. for 1 h. The reaction was quenched with saturated NH4Cl solution and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (0.3 g, 58%).

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with DCM as the eluent

Sources & evidence

ORD record
ord-fe13ca0ea02f414ab50d65eaf24e1a38
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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