4-Methoxybenzylamine → HCID 86685350, compound

HRID 570679Notes

Reaction equation

HRID 570679 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:12])[N:3]=1.C(=O)([O-])O.[Na+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>[Cu]I.CN(C)C=O>[Cl:12][C:4]1[N:3]=[C:2]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 754524-MethoxybenzylamineHCID 516892Sodium BicarbonateHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Product 1

HCID 86685350HCID 86685350, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2,6-dichloropyridine-3-carboxylate (2.06 g), sodium hydrogen carbonate (1.26 g), 4-methoxybenzylamine (1.50 ml), copper(I) iodide (190 mg) and N,N-dimethylformamide (20 ml) was heated to 80° C., and the mixture was stirred for 1 hr and 30 min. The reaction mixture was concentrated under reduced pressure, the obtained residue was diluted with ethyl acetate (150 ml), and the insoluble solid was removed by filtration. To the filtrate was 28% aqueous ammonia (5 ml), and the mixture was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained yellow oil residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.58 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe obtained residue was diluted with ethyl acetate (150 ml)
  3. customthe insoluble solid was removed by filtration
  4. washthe mixture was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained yellow oil residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5f62854505bc40e49aef0d4e0668eb59
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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