Potassium Carbonate → N-(5-Bromo-pyridin-2-ylmethyl)-O-methyl-hydroxylamine

HRID 1487470Notes

Reaction equation

HRID 1487470 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]Cl)=[N:6][CH:7]=1.Cl.[CH3:11][O:12][NH2:13].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:13][O:12][CH3:11])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 114015015-bromo-2-(chloromethyl)pyridine

Product 1

HCID 78955627N-(5-Bromo-pyridin-2-ylmethyl)-O-methyl-hydroxylamineYield 28.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-Bromo-2-chloromethyl-pyridine (2 g, 9.709 mmol) in dimethylformamide (30 mL) is added methoxy amine hydrochloride salt (0.973 g, 11.65 mmol) and K2CO3 (3.35 g, 24.27 mmol) at room temperature then heated to 60° C. for 16 hours. Reaction mixture diluted with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by combiflash using 30% ethyl acetate in hexane as an eluent to afford the title compound (0.6 g). 1HNMR (400 MHz, DMSO-d6) δ: 3.36 (s, 3H), 3.99 (d, J=5.88 HZ, 2H), 7.10 (t, 1H), 7.44-7.46 (dd, J1=8.32 Hz, J2=0.32 Hz, 1H), 7.99-8.02 (dd, J1=2.44 Hz, J2=8.4 Hz, 1H), 8.60-8.61 (dd, J1=2.4 Hz, J2=0.4 Hz, 1H). LC-MS (m/z): [M+H]=217.1.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic layer is dried over sodium sulphate, solvent
  4. customis evaporated in vacuo
  5. custompurified by combiflash

Sources & evidence

ORD record
ord-03722260ab514718a75a43f05dc734db
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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