Water → HCID 20096584, compound

HRID 1769973Notes

Reaction equation

HRID 1769973 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH2:11])([O-:3])=[O:2].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.O>C1(C)C(C)=CC=CC=1>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([N:10]=[CH:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 680234-FluorobenzaldehydeHCID 43383702-Nitro-4-phenylenediamine

Product 1

HCID 20096584HCID 20096584, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 15.3 g (100 mmol) 2-nitro-p-phenylenediamine and 13.6 g (110 mmol) 4-fluorobenzaldehyde in 400 ml xylene is heated under reflux in the presence of 0.5 g of an acid ion exchanger (for example Nafion) for 3 hours in a water separator. Insoluble constituents are filtered out hot and the mixture is allowed to stand overnight at room temperature. An orange-yellow solid crystallizes out. This solid is suction filtered, washed with a little toluene and dried in a vacuum. 22.0 g (85% of theory) 2-amino-5-(4-fluorobenzylideneamino)-nitrobenzene is obtained as orange-yellow crystals.

Workup

  1. filtrationInsoluble constituents are filtered out hot
  2. customAn orange-yellow solid crystallizes out
  3. filtrationfiltered
  4. washwashed with a little toluene
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-7f3bcdb052a14d218c88e6c4ba70a327
Source dataset
uspto-grants-1995_01
Patent number
US05384330

Reaction notes

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