Dimethylformamide dimethyl acetal → 3,9-Dimethyl-beta-carboline

HRID 569023Notes

Reaction equation

HRID 569023 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH3:15]OC(OC)N(C)C.N1(C2CCCCCCC2)CCCCCCN1>CN(C)C=O>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:15])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 133151033-Methyl-9h-pyrido[3,4-b]indoleHCID 66583054Diazabicyclooctane

Product 1

HCID 133151043,9-Dimethyl-beta-carboline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.182 g of 3-methyl-β-carboline (example 5), 0.5 ml of N,N-dimethylformamide-dimethylacetal (90%) and 0.02 g of diazabicyclooctane (Dabco) are stirred in 30 ml of absolute N,N-dimethylformamide for 15 hours at 110° C. The solvent is distilled off under vacuum and the residue is chromatographed on silica gel. (Methylene chloride/ethanol: 9+1). 0.095 g of 3,9-dimethyl-β-carboline with a 134° C. melting point (decomposition) is obtained.

Workup

  1. distillationThe solvent is distilled off under vacuum
  2. customthe residue is chromatographed on silica gel
  3. customwith a 134° C.
  4. customis obtained

Sources & evidence

ORD record
ord-b8750ec4c71049779173d6fd74688f96
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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