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

HRID 1272800Notes

Reaction equation

HRID 1272800 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[CH:10]=O.O.[NH2:13][NH2:14]>>[NH:13]1[C:2]2[C:3](=[CH:4][C:5]([C:8]#[N:9])=[CH:6][CH:7]=2)[CH:10]=[N:14]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 109097255-Cyano-2-fluorobenzaldehyde

Product 1

HCID 111263841H-Indazole-5-carbonitrileYield 81%

Procedure

4-Fluoro-3-formylbenzenecarbonitrile (4.6 g, 30.85 mmol) was suspended in 20 mL of hydrazine mono-hydrate and the reaction mixture was stirred at room temperature for 48 hours. The title compound was isolated by filtration as a white solid, was washed with small portions of distilled water, and was dried in a vacuum (3.6 g, 81% yield). The same protocol was used to convert 3.5 g of 4-fluoro-3-formylbenzenecarbonitrile to the title compound and resulted in the isolation of 1.9 g of white solid (80% yield): 1H NMR (CDCl3) δ 10.45 (br s, 1H), 8.20 (d, 1H), 8.19 (d, 1H), 7.6 (s, 1H); ES-MS 250 [M+1]+.

Sources & evidence

ORD record
ord-a67883488e9b4342b9249ff51b663c08
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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