3-(Trifluoromethyl)benzaldehyde → 5-Nitro-2-phenoxy-benzoic acid (3-trifluoromethyl-benzylidene)-hydrazide

HRID 1791401Notes

Reaction equation

HRID 1791401 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([CH:13]=1)[C:9]([NH:11][NH2:12])=[O:10])([O-:3])=[O:2].[F:21][C:22]([F:32])([F:31])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O>>[F:21][C:22]([F:31])([F:32])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=[N:12][NH:11][C:9](=[O:10])[C:8]1[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[O:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 693558375-Nitro-2-phenoxy-benzoic acid hydrazide

Product 1

HCID 853315215-Nitro-2-phenoxy-benzoic acid (3-trifluoromethyl-benzylidene)-hydrazide

Procedure

A mixture of 5-nitro-2-phenoxy-benzoic acid methyl ester (4.0 g, 14.7 mmol) and hydrazine (5 mL, 80%) was refluxed for 4 h to yield 5-nitro-2-phenoxy-benzoic acid hydrazide (2.97 g, 74%). The title compound was prepared from 5-nitro-2-phenoxy-benzoic acid hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure similar to Example 22. 1H NMR (DMSO-d6): 12.20 (s, 1H), 8.52 (s, 1H), 8.43 (s, 1H), 8.35 (d, J=7.2 Hz, 1H), 8.17 (s, 1H), 8.10 (d, J=6.6 Hz, 1H), 7.81 (m, 1H), 7.75 (t, J=6.6 Hz, 1H), 7.54 (t, J=7.2 Hz, 1H), 7.35 (m, 2H), 7.27 (d, J=7.2 Hz, 1H), 7.03 (m, 2H).

Sources & evidence

ORD record
ord-9c64b1bf0b934a24895eec8674a24d96
Source dataset
uspto-grants-2006_07
Patent number
US07074813B2

Reaction notes

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