Acetic Anhydride → N-(3,5-dichloro-4-cyanopyridin-2-yl)-N-o-tolylacetamide

HRID 81050Notes

Reaction equation

[Cl:1][C:2]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[N:8][CH:7]=[C:6]([Cl:18])[C:3]=1[C:4]#[N:5].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[Cl:1][C:2]1[C:9]([N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:19](=[O:21])[CH3:20])=[N:8][CH:7]=[C:6]([Cl:18])[C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 66926890HCID 66926890, compound

Product 1

HCID 66927080N-(3,5-dichloro-4-cyanopyridin-2-yl)-N-o-tolylacetamideYield 87%

Conditions

Temperature: 180 °C

Procedure

A mixture of 3,5-dichloro-2-(o-tolylamino)isonicotinonitrile (700 mg, 2.52 mmol) and acetic anhydride (10 mL, 106 mmol) was heated in a sealed tube to 180° C. for 20 h. The mixture was cooled to room temperature and concentrated. Silica gel chromatography, loading with dichloromethane-hexanes (1:1) and eluting with 5 to 30% ethyl acetate in hexanes, gave N-(3,5-dichloro-4-cyanopyridin-2-yl)-N-o-tolylacetamide (700 mg, 87% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.44 (1H, s), 7.28-7.43 (4H, m), 2.41 (3H, br. s), 2.04 (3H, s); MS (ES+) m/z: 320 (M+H); LC retention time: 3.38 min (analytical HPLC Method A).

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated
washeluting with 5 to 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-9f99ca7609854aa897d664cfe64e2b9a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846673B2

Reaction notes

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