4-Nitrobenzaldehyde → HCID 59427359, compound

HRID 1013703Notes

Reaction equation

HRID 1013703 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](S(C3C=CC=CC=3)=O)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C1([Mg]Cl)C=CC=CC=1.[N+:29]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[O:37])=[CH:34][CH:33]=1)([O-:31])=[O:30]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH:36]([C:35]3[CH:34]=[CH:33][C:32]([N+:29]([O-:31])=[O:30])=[CH:39][CH:38]=3)[OH:37])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 59427334HCID 59427334, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 59427359HCID 59427359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-methoxy-4-(phenylsulfinyl)quinoline (0.232 g, 0.819 mmol) in THF (6 mL) at −78° C. was added phenylmagnesium chloride, 2.0 M in THF (0.819 ml, 1.64 mmol). After 5 min, the solution was warmed to RT for 15 minutes. The solution was cooled to −78° C. and treated with 4-nitrobenzaldehyde (0.371 g, 2.46 mmol). After 5 min, the solution was warmed to RT. After 1 hr, the reaction was quenched with saturated NH4Cl. The mixture was diluted with CH2Cl2 and washed with water and brine. The organic fraction was dried with Na2SO4 and concentrated in vacuo. The yellow residue was purified by silica gel chromatography using 20-100% Hexanes:EtOAc to afford (7-methoxyquinolin-4-yl)(4-nitrophenyl)methanol as a white solid. MS found M+H+=311.2.

Workup

  1. temperatureThe solution was cooled to −78° C.
  2. waitAfter 5 min
  3. temperaturethe solution was warmed to RT
  4. waitAfter 1 hr
  5. customthe reaction was quenched with saturated NH4Cl
  6. additionThe mixture was diluted with CH2Cl2
  7. washwashed with water and brine
  8. dry with materialThe organic fraction was dried with Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe yellow residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4dd7a28a24a442a8a935fbfe1fdef371
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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