4-Nitrobenzaldehyde → N-(4-nitrobenzylidene)-N'-(4-trifluoromethoxyphenyl)-hydrazine

HRID 1503161Notes

Reaction equation

HRID 1503161 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:12][C:13]([F:24])([F:23])[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1>CCO>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:22][NH:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][C:13]([F:12])([F:24])[F:23])=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 605908[4-(trifluoromethoxy)phenyl]hydrazine

Product 1

HCID 67519187N-(4-nitrobenzylidene)-N'-(4-trifluoromethoxyphenyl)-hydrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of 4-nitrobenzaldehyde (1.57 g, 10.41 mmoL) dissolved in EtOH (21 mL) was added (4-(trifluoromethoxy)phenyl)-hydrazine (2 g, 10.41 mmoL) and the reaction was stirred at room temperature overnight. The solvent was concentrated under reduced pressure and dried under high vacuum to give the title compound as a mixture of E and Z-isomers (3.35 g, 99%): 1H NMR (400 MHz, CDCl3) δ 10.17 (s, 1H), 8.40 (d, J=8.6 Hz, 2H, isomer A), 8.24 (d, J=8.6 Hz, 2H, isomer B), 8.08 (d, J=8.7 Hz, 2H, isomer A), 7.79-7.74 (m, 4H, mixture of isomers A & B), 7.19-7.13 (m, 6H, mixture of isomers A & B); 19F NMR (376 MHz, CDCl3) δ −58.34; ESIMS m/z 325 ([M+H])+.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-b0c2cc513b824c1594d37ca3791e3bc2
Source dataset
uspto-grants-2015_12
Patent number
US09212150B2

Reaction notes

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