Morpholine → 4-(6-Methyl-5-nitro-2-pyridinyl)morpholine

HRID 594098

Reaction equation

Br[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C(O)C>[CH3:8][C:6]1[N:7]=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-bromo-2-methyl-3-nitropyridine (2.05 g, 9.45 mmol) in ethanol (10 mL) was added morpholine (1.728 mL, 19.84 mmol) and the reaction mixture was stirred at 70° C. for 5 hours. The reaction mixture was allowed to cool to room temperature causing a precipitate. The solid was collected by filtration and washed with ethanol (5 mL), then dried in vacuo. The crude was redissolved in a mixture of saturated sodium carbonate solution and ethyl acetate. The organic phase was separated, washed with further saturated sodium carbonate solution, then dried over magnesium sulphate and evaporated in vacuo to give the title compound (1.47 g) as a yellow solid. LCMS (2 min, formic) Rt 0.92 min, m/z (ES+) 224 (M+H).

Workup

temperatureto cool to room temperature
filtrationThe solid was collected by filtration
washwashed with ethanol (5 mL)
customdried in vacuo
dissolutionThe crude was redissolved in a mixture of saturated sodium carbonate solution and ethyl acetate
customThe organic phase was separated
washwashed with further saturated sodium carbonate solution
dry with materialdried over magnesium sulphate
customevaporated in vacuo

Sources & evidence

ORD record: ord-456d0803c97f4b36b810f7a4623636de
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Linked notes

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