1,2-Dichloroethane → N-methyl-N-methoxy-3-(2-pyridyl)-phenylacetamide

HRID 840740Notes

Reaction equation

HRID 840740 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:30]=[C:31]([CH2:35][C:36](O)=[O:37])[CH:32]=[CH:33][CH:34]=1.C(Cl)CCl.C([O-])(O)=O.[Na+]>CN(C=O)C.[Cl-].[Na+].O.CCOC(C)=O>[CH3:5][N:4]([O:3][CH3:2])[C:36](=[O:37])[CH2:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)[CH:30]=1

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 120760552-(3-(Pyridin-2-yl)phenyl)acetic acid

Product 1

HCID 22620144N-methyl-N-methoxy-3-(2-pyridyl)-phenylacetamideYield 88.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of N-methoxy-N-methylamine hydrochloride (0.980 g, 10.0 mmol) in DMF (25 mL) was added N-methylmorpholine (1.21 mL, 11.0 mmol), HOBt (1.50 g, 11.1 mmol), 3-(2-pyridyl)-phenylacetic acid (2.36 g, 11.1 mmol), and EDC (2.13 g, 11.1 mmol). The reaction was stirred overnight whereupon it was poured into a rapidly-stirred mixture of 150 mL each of EtOAc, 10% NaHCO3, and brine. After stirring for 30 min, the layers were separated and the aqueous layer was washed with fresh EtOAc (150 mL). The combined organic layers were washed with 10% Na2CO3, and brine, then dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, 3:1 EtOAc:hexane) gave 2.275 g of the title compound: MS (ES+) (MH+) 257.2.

Workup

  1. stirringAfter stirring for 30 min
  2. customthe layers were separated
  3. washthe aqueous layer was washed with fresh EtOAc (150 mL)
  4. washThe combined organic layers were washed with 10% Na2CO3, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b0aebf3f1ed4b7d99ba05a81fad5c8f
Source dataset
uspto-grants-2002_04
Patent number
US06369077B1

Reaction notes

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