Methyl iodide → 2-(4-Chloro-5-methoxy-1H-indol-3-yl)acetonitrile

HRID 1898994Notes

Reaction equation

CN([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[C:12]=2[Cl:14])[NH:7][CH:6]=1)C.[C-:17]#[N:18].[K+].CI>>[C:17]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[C:12]=2[Cl:14])[NH:7][CH:6]=1)#[N:18]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 9032Potassium Cyanide

HCID 233730563-Dimethylaminomethyl-4-chloro-5-methoxy-indole

Product 1

HCID 233730472-(4-Chloro-5-methoxy-1H-indol-3-yl)acetonitrileYield 91.2%

Procedure

Reaction of 3-dimethylaminomethyl-4-chloro-5-methoxy-indole (2.00 g, 8.40 mmol) with potassium cyanide (2.08 g, 32.0 mmol) and methyl iodide (4.72 g, 33.0 mmol) and subsequent workup as described in 1 (d) gave 3-cyanomethyl-4-chloro-5-methoxyindole (1.69 g), m.p. 138°-9° C.

Sources & evidence

ORD record: ord-3c69a911ba344ad0b0fe9b2eb2dc98f5
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571833

Reaction notes

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