Hydrazine → 5-Nitro-2-phenoxy-benzoic acid hydrazide

HRID 2084277Notes

Reaction equation

HRID 2084277 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:21][NH2:22]>>[N+:10]([C:8]1[CH:7]=[CH:6][C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH:9]=1)[C:3]([NH:21][NH2:22])=[O:2])([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 23019067HCID 23019067, compound

Product 1

HCID 693558375-Nitro-2-phenoxy-benzoic acid hydrazideYield 74%

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).

Workup

  1. temperaturewas refluxed for 4 h

Sources & evidence

ORD record
ord-9e2f1a9bc2f84b6e8db17d1ee2ba4244
Source dataset
uspto-grants-2004_04
Patent number
US06716859B2

Reaction notes

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