Acetic Acid → 3-Methyl-9h-pyrido[3,4-b]indole

HRID 569022

Reaction equation

HRID 569022 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[I-].[Na+].Cl[Si](C)(C)C.C(O)(=O)C>CN(C)C=O.[Zn]>[CH3:2][C:3]1[N:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 53533383-Hydroxymethyl-beta-carboline

Product 1

HCID 133151033-Methyl-9h-pyrido[3,4-b]indole

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2 g of 3-hydroxymethyl-β-carboline, 3.7 g of sodium iodide and 2.5 ml of chlorotrimethylsilane are stirred in 50 ml of N,N-dimethylformamide at a bath temperature of 35° C. for 4 hours. 3 g of zinc powder and 10 ml of glacial acetic acid are added to the resulting yellow suspension and stirred for another 18 hours at 80° C. The reaction mixture is allowed to clarify on Celite and the filtrate is concentrated under vacuum. The resulting oil is chromatographed on silica gel (methylene chloride/ethanol: 9+1). 0.825 g of 3-methyl-β-carboline with a 255°-256° C. melting point was obtained.

Workup

  1. concentrationthe filtrate is concentrated under vacuum
  2. customThe resulting oil is chromatographed on silica gel (methylene chloride/ethanol: 9+1)
  3. customwith a 255°-256° C.
  4. customwas obtained

Sources & evidence

ORD record
ord-221c279277004ba281c77d9f81cbdb36
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Linked notes

Loading…