Methyl iodide → 6-Chloro-N-(4-ethoxy-2-nitrophenyl)-N-methyl-3-pyridinecarboxamide

HRID 1007204

Reaction equation

HRID 1007204 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])=[O:9])=[CH:4][CH:3]=1.[CH3:23][O-].[Na+].IC>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])[CH3:23])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 98401276-Chloro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamideHCID 10942334Sodium Methoxide

Product 1

HCID 99022846-Chloro-N-(4-ethoxy-2-nitrophenyl)-N-methyl-3-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamide (50 mg, 0.155 mmol) in DMF (2 ml) was added sodium methoxide (12 mg, 0.222 mmol) in DMF (1 ml) and the reaction mixture was stirred for 10 min. To the mixture was added iodomethane (22 mg, 0.155 mmol) slowly and the mixture was stirred for at room temperature for 3 h. It was diluted with ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by column chromatography to yield the titled compound as a light brown liquid. 1H NMR (CDCl3): 8.17 (d, J=2.1, 1H), 7.68-7.65 (m, 1H), 7.35 (d, J=2.7, 1H), 7.21 (t, J=7.8, 2H), 7.10-7.06 (m, 1H), 4.08-4.01 (m, 2H), 3.40 (s, 3H), 1.44 (t, J=6.9, 3H).

Workup

  1. stirringthe mixture was stirred for at room temperature for 3 h
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2e9b5a0cb09742b5b398e9734a4ad3dd
Source dataset
uspto-grants-2004_09
Patent number
US06794397B2

Linked notes

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