Diethyl Pyrocarbonate → 2-chloro-N-methoxy-N,6-dimethylpyridine-3-carboxyamide

HRID 906329Notes

Reaction equation

HRID 906329 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1C(O)=O.Cl.[CH3:13][NH:14][O:15][CH3:16].C(N(CC)C(C)C)(C)C.CCOC(OC([O:34][CH2:35][CH3:36])=O)=O>O1CCCC1.O>[Cl:1][C:2]1[C:3]([CH2:36][C:35]([N:14]([O:15][CH3:16])[CH3:13])=[O:34])=[CH:7][CH:8]=[C:9]([CH3:11])[N:10]=1

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 1317283202-chloro-N-methoxy-N,6-dimethylpyridine-3-carboxyamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-6-methylnicotinic acid (1.00 g, 5.83 mmol) in tetrahydrofuran (10 mL) was successively added with N,O-dimethylhydroxyamine hydrochloride (910 mg, 9.33 mmol), N,N-diisopropylethylamine (3.00 g, 23.2 mmol) and DEPC (1.43 g, 8.77 mmol) on an ice bath, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 2-chloro-N-methoxy-N,6-dimethylpyridine-3-carboxyamide as colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ae87d72284e04634966872cc5f65e5ee
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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