Ammonium Chloride → N-(6-aminopyridin-3-yl)methanesulfonamide

HRID 719869Notes

Reaction equation

HRID 719869 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>CO.O.[Zn]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 15567564N-(6-nitropyridin-3-yl)methanesulfonamide

Product 1

HCID 21897349N-(6-aminopyridin-3-yl)methanesulfonamideYield 76.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-(6-nitro-pyridin-3-yl)-methanesulfonamide (298 mg, 1.37 mmol) in methanol (8.3 mL) was treated with a solution of ammonium chloride (154 mg, 2.88 mmol) in water (1 mL). This solution was stirred at 25° C. for 5 min. At this time, zinc dust (879 mg, 13.44 mmol) was added to the reaction. The resulting reaction mixture was then heated under reflux for 3 h. At this time, the reaction was cooled to 25° C. and then was filtered through a pad of celite (9/1 methylene chloride/methanol wash). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 9/1 methylene chloride/methanol) afforded N-(6-amino-pyridin-3-yl)-methanesulfonamide (196.3 mg, 76.4%) as a reddish-brown oil: EI-HRMS m/e calcd for C6H9N3O2S (M+) 184.0415, found 184.0415.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureunder reflux for 3 h
  4. temperatureAt this time, the reaction was cooled to 25° C.
  5. filtrationwas filtered through a pad of celite (9/1 methylene chloride/methanol wash)
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b9fefb650dd4438882c56b28ed89f80d
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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