Toluene → HCID 178484919, compound

HRID 228275Notes

Reaction equation

Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Al](C)(C)C.C1(C)C=CC=CC=1.[ClH:21].[CH3:22][NH2:23]>>[CH3:22][NH:23][C:4](=[NH:5])[C:3]1[CH:6]=[CH:7][C:8]([Cl:21])=[N:9][CH:2]=1

Participants

Reactant 4

HCID 1140Toluene

HCID 810792-Chloronicotinonitrile

HCID 6364545Methylamine hydrochloride

HCID 16682925Trimethylaluminum

Product 1

HCID 178484919HCID 178484919, compoundYield 76.7%

Procedure

Using a method similar to Example 380, Part D, using 2-chloronicotinonitrile (1.00 g, 7.32 mmol), 2.0 M Al(CH3)3 in toluene (11 mL, 22.0 mmol) and methylamine hydrochloride (1.48 g, 22.0 mmol) gives the title compound (0.952 g, 76.7%): MS ES+ 171.8 (M+H)+, MS ES− 168.0 (M−H)−; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95% over 19 min], tR=5.0 min, 97.0% purity.

Sources & evidence

ORD record: ord-99ea018e4c7b410e9de246c0a6d73551
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560463B2

Reaction notes

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