Hydrazine hydrate (1:1) → 4-Fluorobenzohydrazide

HRID 2406422Notes

Reaction equation

HRID 2406422 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9]C=[N:11][N:12]=2)=[CH:4][CH:3]=1.FC1C=CC(CCC([O-])=O)=CC=1.O.NN>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:12][NH2:11])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 6927183HCID 6927183, compoundHCID 17951329HCID 17951329, compound

Product 1

HCID 99724-Fluorobenzohydrazide

Procedure

In one embodiment, 2-(4-fluorophenyl)-1,3,4-oxadiazole may be prepared as provided in Scheme 11A. In this case, 4-fluoro-phenyl-ethylformate is reacted with hydrazine hydrate to provide 4-fluorobenzohydrazide. This intermediate is then reacted with triethylorthoformate to provide 2-(4-fluorophenyl)-1,3,4-oxadiazole. 2-(4-Fluorophenyl)-1,3,4-oxadiazole may then be converted to a compound of formula (I-A) by the methods described herein.

Workup

  1. customas provided in Scheme 11A

Sources & evidence

ORD record
ord-49c5e9aea9de4dd2999ed6039241c4ce
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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