(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 2233340Notes

Reaction equation

HRID 2233340 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>C(Cl)Cl.O=[Mn]=O>[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

4

Reactant 1

HCID 21873770(2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

Product 1

HCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeYield 61%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethanol (250 mg, 1.5 mmole) in CH2Cl2 (5 mL) was treated with MnO2 (650 mg, 7.5 mmole). After 3 days the mixture was filtered and the filtrate was concentrated to afford the title compound (150 mg, 61%) as a white solid: MS (APCI+) m/e 166 (M+H)+.

Workup

  1. filtrationAfter 3 days the mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-15888ed1e1ce4b06ac98bc393fb0ea2d
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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