3-Nitrobenzaldehyde → HCID 178426385, compound

HRID 1036949Notes

Reaction equation

HRID 1036949 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[CH:6][CH:7]=1.[N+:9]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O)([O-:11])=[O:10]>C(O)C>[N+:9]([C:12]1[CH:13]=[C:14](/[CH:15]=[N:8]/[C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:17]=[CH:18][CH:19]=1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 7813p-Toluidine

Product 1

HCID 178426385HCID 178426385, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of p-tolylamine (21.43 g, 0.2 mol) in ethanol (300 mL) was added 3-Nitro-benzaldehyde (30.22 g, 0.2 mol). The mixture was stirred overnight at room temperature. After filtration, the yellow solid was dried under infrared lamp, and the filtrate was concentrated, treated with ethanol again. The precipitated solid was filtered to afford 44.5 g of [1-(3-nitro-phenyl)-meth-(E)-ylidene]-p-tolyl-amine (Yield: 93%).

Workup

  1. filtrationAfter filtration
  2. customthe yellow solid was dried
  3. concentrationthe filtrate was concentrated
  4. additiontreated with ethanol again
  5. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-76952948b4c74e968b2799a24e60372c
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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