5-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-methanol → 5-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carbaldehyde

HRID 1720329Notes

Reaction equation

HRID 1720329 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:22][O:23][CH3:24])=[C:11]([CH2:20][OH:21])[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:22][O:23][CH3:24])=[C:11]([CH:20]=[O:21])[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 224177505-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-methanol

Product 1

HCID 224177275-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carbaldehydeYield 74.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

1.3 g (0.00354 mol) of 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-methanol is stirred for 192 hours under argon at room temperature with 1.74 g (0.02 mol) of manganese dioxide in 200 ml of dichloromethane. The manganese dioxide is suctioned off, the filtrate concentrated by evaporation and the residue recrystallized from ethanol. Thus 0.96 g (74% of theory) of 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carbaldehyde is obtained, melting point 248°-250° C.

Workup

  1. concentrationthe filtrate concentrated by evaporation
  2. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-ba4498f838774ca18d0b577d1f4c0acd
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

Loading…