Sodium Cyanide → HCID 178510964, compound

HRID 1743357Notes

Reaction equation

HRID 1743357 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1.[C-:14]#[N:15].[Na+]>CN(C)C=O>[C:14]([CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1)#[N:15]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 178478460HCID 178478460, compound

Product 1

HCID 178510964HCID 178510964, compoundYield 449.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of (3-chloropropyl)indazole (Sasakura et al, Synth. Comm., 18, pg 259 (1988)) (750 mg, 3.75 mM) in dimethylformamide (25 ml) was stirred at room temperature and sodium cyanide (370 mg, 7.5 mM) added in one portion. The resulting mixture was heated at 90° C. for 4 hr. The dimethylformamide was removed in vacuo and the residue partitioned between water and ethyl acetate. The combined organics were dried over magnesium sulfate. Column chromatography (ethyl acetate/cyclohexane, 1:1) provided 3-(3-cyanopropyl)indazole as a clear oil (3.21 g, 83%).

Workup

  1. customThe dimethylformamide was removed in vacuo
  2. customthe residue partitioned between water and ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulfate

Sources & evidence

ORD record
ord-6bbee1f3abe24a2ab5e8a919f1939faa
Source dataset
uspto-grants-2006_03
Patent number
US07009056B2

Reaction notes

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