3-Nitrobenzaldehyde → HCID 178510045, compound

HRID 1036960Notes

Reaction equation

HRID 1036960 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O)([O-:12])=[O:11]>C1(C)C=CC=CC=1>[N+:10]([C:13]1[CH:14]=[C:15](/[CH:16]=[N:1]/[C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH:18]=[CH:19][CH:20]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 133964-Aminobenzonitrile

Product 1

HCID 178510045HCID 178510045, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 4-amino-benzonitrile (23.6 g, 0.2 mmol) in toluene (200 mL) was treated with a solution of 3-nitro-benzaldehyde (30.2 g, 0.2 mmol) in toluene (50 mL). The resultant mixture was allowed to reflux for 6 h. Toluene was removed under vacuum. The residue was purified by recrystallization from ethanol to afford 4-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-benzonitrile as yellow solid (50 g, yield %: 95.0%).

Workup

  1. temperatureto reflux for 6 h
  2. customToluene was removed under vacuum
  3. customThe residue was purified by recrystallization from ethanol
  4. customto afford

Sources & evidence

ORD record
ord-738c0bda75304e0b9d41e1954a0f9ee5
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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