Formic Acid → N-((5-Chloropyridin-2-yl)methyl)formamide

HRID 246544Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][NH2:10])=[N:7][CH:8]=1.[CH:11](O)=[O:12].[OH-].[NH4+]>O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][NH:10][CH:11]=[O:12])=[N:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (5-chloropyridin-2-yl)methanamine hydrochloride (1.0 g, 5.31 mmol) in formic acid (5.09 g, 4.24 mL, 106 mmol) was refluxed at 110° C. After 20 h the reaction was cooled to 0° C. and 25% ammonium hydroxide in water was added until pH˜9 was reached. The mixture was diluted with water and then extracted into dichloromethane (3×). The organic layers were combined and dried (MgSO4), filtered and concentrated in vacuo. This was used directly in the next step without further purification. 1H NMR (CDCl3) δ: 8.53 (s, 1H), 8.35 (s, 1H), 7.69 (m, 1H), 7.65 (m, 1H), 4.64 (d, J=5.3 Hz, 2H), 4.0 (s, 1H).

Workup

extractionextracted into dichloromethane (3×)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThis was used directly in the next step without further purification

Sources & evidence

ORD record: ord-b8a295100b1d4966955f94719da42a77
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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