Nitromethane → HCID 68630899, compound

HRID 1908257Notes

Reaction equation

HRID 1908257 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.[OH-].[K+].[N+:17]([CH3:20])([O-:19])=[O:18]>C1COCC1.CO>[N+:17]([CH2:20][CH:11]([C:10]1[CH:9]=[CH:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:14][CH:13]=1)[OH:12])([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 14797Potassium HydroxideHCID 15152404-Pyridin-2-ylbenzaldehyde

Product 1

HCID 68630899HCID 68630899, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution consisting of 4-pyridin-2-yl-benzaldehyde (346 mg, 1.9 mmol) in THF (5 mL) and NO2CH3 (0.3 mL) and MeOH (2.5 mL) was added KOH (2.5 M, 1.13 mL). The reaction mixture was stirred at 0° C. for 30 min. and then quenched with a saturated NH4Cl solution. The aqueous mixture was extracted with EtOAC. The organic layer was dried (Na2SO4) and concentrated. The crude residue was purified (FCC) to give the title compound (257 mg, 60%).

Workup

  1. customquenched with a saturated NH4Cl solution
  2. extractionThe aqueous mixture was extracted with EtOAC
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-37dedd1c469b4ca199121d3cadfc335f
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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