HCID 68089387, compound → HCID 86667807, compound

HRID 1772011Notes

Reaction equation

HRID 1772011 reaction equation
[CH3:1][N:2]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[N:7]3)[N:4]=[C:3]1[CH2:15][OH:16]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[N:7]3)[N:4]=[C:3]1[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 68089387HCID 68089387, compound

Product 1

HCID 86667807HCID 86667807, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-methyl-3H-imidazo[4,5-f]quinoxalin-2-yl)methanol (880 mg, 4.03 mmol) in DCM (100 mL) was added activated manganese (IV) dioxide (3.5 g, 40.3 mmol). The mixture was stirred at room temperature for 16 h. Then the mixture was filtered and the filtrate was concentrated under reduce pressure to give the crude product, which was purified by silica gel column (eluting with DCM/MeOH v/v 30:1) to give 3-methyl-3H-imidazo[4,5-f]quinoxaline-2-carbaldehyde as a yellow solid (310 mg, yield 36%). ESI MS: m/z 213.0 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 10.25 (s, 1H), 9.02 (d, J=2.0 Hz, 1H), 8.95 (d, J=2.4 Hz, 1H), 8.15 (d, J=9.2 Hz, 1H), 7.88 (d, J=9.2 Hz, 1H), 4.33 (s, 3H).

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas purified by silica gel column (
  5. washeluting with DCM/MeOH v/v 30:1)

Sources & evidence

ORD record
ord-dc9ecda15f0d42418051c3066b818629
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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