Hydrazine hydrate (1:1) → 1H-Indazole-5-carbonitrile

HRID 2189732Notes

Reaction equation

HRID 2189732 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](F)[CH:6]=[C:7]([CH:10]=1)[CH:8]=O)#[N:2].O.[NH2:13][NH2:14]>>[NH:13]1[C:6]2[C:7](=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:8]=[N:14]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 447549173-Fluoro-5-formylbenzonitrile

Product 1

HCID 111263841H-Indazole-5-carbonitrile

Procedure

5-Cyano-3-fluorobenzaldehyde (4 g, 26.8 mmol) was dissolved in hydrazine hydrate and stirred at room temperature for 18 hours. The solution was poured onto ice and the resultant solid was separated by filtration and then dried under vacuum at 60° C. to afford the title compound (1.27 g) as a pink solid. Further material was isolated from the aqueous layer. MS (ES): C8H5N3 requires 143; found 144 (MH+).

Workup

  1. additionThe solution was poured onto ice
  2. customthe resultant solid was separated by filtration
  3. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-fed1136edbaf4a77ab82c1c5925cf629
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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