Water → HCID 57815225, compound

HRID 385497Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH2:7].Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=1.C(OCC)(=O)C.O>CN(C)C=O.C(N(CC)CC)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1.1 g of 1-(1,3-dioxolan-2-yl)methanamine in 10 mL of N,N-dimethylformamide, 1.6 mL of triethylamine and 2.0 g of 2-chloro-6-methoxy-3-nitropyridine were added at room temperature, and the mixture was stirred at 55 to 65° C. for 1 hour. The reaction mixture was cooled to room temperature, and ethyl acetate and water were then added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.7 g of N-(1,3-dioxolan-2-ylmethyl)-6-methoxy-3-nitropyridin-2-amine as a yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate
washthe resultant solution was washed sequentially with water
dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-46b806dfa52d4705a6c0b30d242e9c83
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367831B2

Reaction notes

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