(2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol → 2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde

HRID 1804726Notes

Reaction equation

[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][OH:12])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1>O1CCCC1.[O-2].[O-2].[Mn+4]>[O:1]1[C:10]2[CH:9]=[C:8]([CH:11]=[O:12])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 111 g of (2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl)methanol in 1110 mL of tetrahydrofuran, 164 g of manganese dioxide was added, the mixture was stirred for 5 hours at 70° C. and stirred overnight at room temperature. The reaction mixture was subjected to celite filtration and the filter residue was washed with 500 mL of tetrahydrofuran. The filtrate and the wash liquid were combined to evaporate the solvent under reduced pressure. The obtained residue was recrystallized from 750 mL of 2-propanol to give 53.5 g of 2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-carbaldehyde as a light yellow solid.

Workup

stirringstirred overnight at room temperature
filtrationThe reaction mixture was subjected to celite filtration
washthe filter residue was washed with 500 mL of tetrahydrofuran
customto evaporate the solvent under reduced pressure
customThe obtained residue was recrystallized from 750 mL of 2-propanol

Sources & evidence

ORD record: ord-d87676ec7a98426e8d9095e5d1c335a4
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354426B2

Reaction notes

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