Pyridine → N-(2-Methoxy-5-pyridyl)-dichloroacetamide

HRID 231077Notes

Reaction equation

HRID 231077 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[N:12][CH:13]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:3](=[O:4])[CH:2]([Cl:6])[Cl:1])=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6593Dichloroacetyl chlorideHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 14551030N-(2-Methoxy-5-pyridyl)-dichloroacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloroacetyl chloride, 97% (2.0 ml, 0.03 mol) was added over a period of 30 seconds to a mixture of 5-amino-2-methoxypyridine (3.7 g, 0.03 mol), pyridine (5.0 ml) and methylene chloride (100 ml). The reaction was exothermic and allowed to stand at room temperature for one hour. The reaction was then washed with 5% sodium carbonate solution (2×100 ml), dried over anhydrous magnesium carbonate, filtered, and evaporated in vacuo to give a solid that was triturated with hexane to yield 6.4 g of the title compound, m.p. 104°-107° C. The title product was identified by infrared (IR), nuclear magnetic resonance (NMR) and mass spectrocopy (MS) analysis.

Workup

  1. washThe reaction was then washed with 5% sodium carbonate solution (2×100 ml)
  2. dry with materialdried over anhydrous magnesium carbonate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give a solid
  6. customthat was triturated with hexane

Sources & evidence

ORD record
ord-28ccf444c4f54b2c9706641bf7a4d897
Source dataset
uspto-grants-1989_07
Patent number
US04845107

Reaction notes

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