Tin chloride monohydrate → 2-amino-N-(4-chloropyridin-3-yl)benzamide hydrochloride

HRID 44240

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O.O.[Sn](Cl)(Cl)(Cl)Cl>O1CCOCC1>[ClH:1].[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([NH:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:19]

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of N-(4-chloropyridin-3-yl)-2-nitrobenzamide (1.9 g, 6.8 mmol) in dioxane (10 mL) and conc. HCL (40 mL) was treated with tin chloride hydrate (6.2 g, 27.2 mmol). The reaction mixture was stirred at 90° C. for one hour (the mixture evolved from suspension to solution and back to suspension). After cooling down, the precipitate was filtered off and dried under high vacuum. The 2-amino-N-(4-chloropyridin-3-yl)benzamide hydrochloride was obtained as an off-white solid (3.0 g). LCMS [M+H]: 248.

Workup

temperatureAfter cooling down
filtrationthe precipitate was filtered off
customdried under high vacuum

Sources & evidence

ORD record: ord-0410ad2bfead440595a292cfa64d8044
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541407B2

Linked notes

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