[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methanol → 9-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carbaldehyde

HRID 992573Notes

Reaction equation

HRID 992573 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([CH2:18][OH:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2>[O-2].[Mn+4].[O-2].ClCCl>[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([CH:18]=[O:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 1

HCID 9928662[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methanol

Product 1

HCID 99285579-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carbaldehydeYield 88.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A 250-mL round-bottomed flask was charged with [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methanol (1.84 g, 5.1 mmol), manganese (IV) oxide (1.14 g, 13.1 mmol) and dichloromethane (60 mL). The reaction mixture was stirred at room temperature for 12 hours. The mixture was filtered, concentrated in vacuo, and the residue chromatographed (hexane:ethyl acetate=10:1), affording the title compound (1.6 g, 87% yield). 1H NMR (CDCl3) δ10.3 (s, 1H), 8.9 (s, 1H), 8.8 (s, 1H), 8.3 (d,1H), 7.7 (t, 1H), 7.5-7.4 (m, 3H), 7.2 (s, 1H), 6.6 (s, 1H), 5.7 (s, 2H), MS (Cl); 355, 357, 359.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue chromatographed (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d67370d347344c26aa7010bf1113aa8b
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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