2,3,4,9-Tetrahydro-4-methyl-1H-pyrido[3,4-b]indole → 4-Methyl-9H-beta-carboline

HRID 552220Notes

Reaction equation

HRID 552220 reaction equation
[CH3:1][CH:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][NH:4][CH2:3]1>[Pd]>[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

3

Reactant 1

HCID 593375522,3,4,9-Tetrahydro-4-methyl-1H-pyrido[3,4-b]indole

Product 1

HCID 593375704-Methyl-9H-beta-carbolineYield 98.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
160 °C

Procedure

4-methyl-2,3,4,9-tetrahydro-1H-β-carboline (214 mg, 1.17 mmol) was suspended in xylenes (10 ml). Pd (10% wt. on carbon, 21 mg) catalyst was added thereto and the reaction mixture was stirred at 160° C. for 24 hours, then cooled to RT and filtered through celite. The filtrate was concentrated to dryness to give 4-methyl-9H-β-carboline (210 mg). 1H-NMR (300 MHz, DMSO-d6): δ 11.73 (br s, 1); 8.78 (br s, 1); 8.19 (d, 1); 8.13 (s, 1); 7.62 (br s, 1); 7.53 (t, 1); 7.25 (t, 1); 2.78 (s, 3). NH4OAc standard conditions. DAD Rf=2.24 min. M+H=183.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-41b1328a68bf44b4a900a49c01c82674
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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