Water → 3,4-Dihydro-2H-pyrido(3,2-b)(1,4)oxazine

HRID 2097086Notes

Reaction equation

[O:1]1[CH2:6][C:5](=O)[NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>C1COCC1>[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cold solution of 4H-pyrido[3,2-b][1,4]oxazin-3-one (5.00 g, 33.3 mmol) in THF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in THF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 0° C. and quenched the reaction with H2O (4 mL) followed by NaOH (4 mL, 15%) and H2O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85%) as a blue-gray powder: 1H NMR (500 MHz, DMSO-d6) δ 7.53 (dd, J=4.5, 1.0 Hz, 1H), 6.90-6.89 (m, 1H), 6.61 (br s, 1H), 6.44 (dd, J=8.0, 3.0 Hz, 1H), 4.08 (t, J=4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e 137 (M+H)+.

Workup

additionthe addition
temperaturethe solution was heated to reflux
customquenched
customthe reaction with H2O (4 mL)
filtrationThe resulting slurry was filtered over Celite
concentrationthe filtrate concentrated

Sources & evidence

ORD record: ord-5db5459f57ce4725b70916b8b07e6176
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450307B2

Reaction notes

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