(8-Methoxyquinolin-5-yl)methanol → 8-Methoxyquinoline-5-carbaldehyde

HRID 2374167Notes

Reaction equation

HRID 2374167 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:14][O:13][C:10]1[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]([CH:2]=[O:1])=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 7172171(8-Methoxyquinolin-5-yl)methanol

Product 1

HCID 71762248-Methoxyquinoline-5-carbaldehydeYield 94.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

5-Hydroxymethyl-8-methoxyquinoline (6.5 g, 34 mmol) from Step 1 was dissolved in 250 mL of DCM and treated with 24 g of manganese dioxide. After stirring for 24 h, the mixture was treated with an additional 6 g of manganese dioxide and stirred for 24 h. The mixture was filtered through a pad of Celite, and the filtrate was concentrated under vacuum to afford 6 g of the title compound as a brown solid. 1H NMR (CDCl3) δ 10.2 (s, 1 H), 9.69 (d, 1 H), 9.01 (d, 1 H), 8.01 (d, 1H), 7.61 (dd, 1H), 7.16 (d, 1H), 4.19 (s, 3H).

Workup

  1. stirringstirred for 24 h
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-33fa23ad14d542c9ae1ca0933b40efa5
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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