Acetic Acid → N-(benzylideneamino)-4-nitroaniline

HRID 1590537Notes

Reaction equation

HRID 1590537 reaction equation
CN([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)CCCCCCCCCCCO.[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=1)([O-:25])=[O:24].C(O)(=O)C>O>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([NH:32][N:33]=[CH:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:22][CH:21]=2)=[CH:30][CH:31]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3310889(4-Nitrophenyl)hydrazineHCID 197672734-[N-methyl-N-(11-hydroxyundecyl)-amino]-benzaldehyde

Product 1

HCID 96671N-(benzylideneamino)-4-nitroanilineYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.62 g of 4-[N-methyl-N-(11-hydroxyundecyl)-amino]-benzaldehyde, 4.33 g of 4-nitrophenylhydrazine and 25 ml of glacial acetic acid were [sic] refluxed for 30 minutes and left to stand overnight at room temperature. 70 ml of ice water were added to the resulting reaction mixture and the mixture was stirred thoroughly After the water had been removed from the reaction mixture, the reaction product, which had now precipitated, was separated off and then subjected to preliminary purification by boiling with active carbon in acetone. The prepurified product was then purified by flash chromatography on silica gel, a mixture of hexane and ethyl acetate in a volume ratio of 6:4 being used as the mobile phase. A total of 3.4 g of 4'-N-methyl-N-(11-hydroxyundecyl)-amino]-benzaldehyde-4-nitrophenylhydrazone were obtained, corresponding to a yield of 28% of theory. In its IR spectrum, this product, in the form of a KBr pellet, had bands at 3,400, 3,250, 1,585, 1,510, 1,490, 1,460, 1,320, 1,290, 1,270, 1,170, 1,100, 830 and 810 cm-1.

Workup

  1. temperaturerefluxed for 30 minutes
  2. waitleft
  3. customhad been removed from the reaction mixture
  4. customthe reaction product, which had now precipitated
  5. customwas separated off
  6. customsubjected to preliminary purification
  7. customThe prepurified product was then purified by flash chromatography on silica gel
  8. additiona mixture of hexane and ethyl acetate in a volume ratio of 6:4

Sources & evidence

ORD record
ord-48bc8f4fdf7942f1a37f2a855c77f372
Source dataset
uspto-grants-1993_04
Patent number
US05204178

Reaction notes

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