Triethylamine → 1H-Indole-7-carbonitrile

HRID 1512723Notes

Reaction equation

[I-].ClC1C=CC=C[N+]=1C.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH:19]=[N:20]O)[CH:12]=[CH:11]1.C(N(CC)CC)C>C1COCC1>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:19]#[N:20])[CH:12]=[CH:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

2-chloro-1-methylpyridinium iodide (1.930 g) was added to a solution of 1H-indole-7-carbaldehyde oxime (D1) (1.1 g) in dry THF (80 mL) at RT. After stirring for 10 min, triethylamine (3.35 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at RT for 2 hours, then was heated to 50° C. and stirred at 50° C. for 2.5 hours. The solvent was evaporated. The residue was dissolved in EtOAc (100 mL) and water (100 mL) was added. The organic fraction was separated, washed with aqueous HCl (0.5 M, 50 mL). The organic fraction was dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford 1H-indole-7-carbonitrile (D2) as a white solid (0.95 g). δH (DMSO-d6, 400 MHz): 6.64 (1H, m), 7.16 (1H, t), 7.56 (1H, m), 7.68 (1H, d), 7.93 (1H, d), 12.02 (1H, br s). MS (ES): C9H6N2 requires 142; found 141.0 (M−H+).

Workup

stirringThe reaction mixture was stirred at RT for 2 hours
stirringstirred at 50° C. for 2.5 hours
customThe solvent was evaporated
dissolutionThe residue was dissolved in EtOAc (100 mL)
additionwater (100 mL) was added
customThe organic fraction was separated
washwashed with aqueous HCl (0.5 M, 50 mL)
dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
concentrationThe dried solution was concentrated

Sources & evidence

ORD record: ord-cde488f9bc7c45b685e30f21a3f4d966
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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