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

HRID 1520468Notes

Reaction equation

HRID 1520468 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-30d0c1a6747a4c55a38a41ea5056916a
Source dataset
uspto-grants-2015_07
Patent number
US09073894B2

Reaction notes

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