2-methyl-6-nitro-2,3,4,9-tetrahydro-1H-beta-carboline → 2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-6-amine

HRID 2383272

Reaction equation

HRID 2383272 reaction equation
[CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:15]([O-])=O)[CH:10]=3)[NH:5][C:4]=2[CH2:3]1>CCO.[Pd]>[NH2:15][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]1[CH2:3][N:2]([CH3:1])[CH2:14][CH2:13][C:12]2=1

Participants

4

Reactant 1

HCID 598434412-methyl-6-nitro-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 598434382-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-6-amineYield 107%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-6-nitro-2,3,4,9-tetrahydro-1H-β-carboline (description 1) (1.42 g, 6.13 mmol) in EtOH (300 mL), 570 mg of (5%) Pd/C were added. The mixture was hydrogenated under 20 psi at room temperature for 20 h and filtered through a pad of Celite. The EtOH was evaporated to dryness to yield 1.32 g of 6-amino-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline that were used directly to synthesize compounds of formula I.

Workup

  1. filtrationfiltered through a pad of Celite
  2. customThe EtOH was evaporated to dryness

Sources & evidence

ORD record
ord-22b91244e89a41949e5896ad7360e274
Source dataset
uspto-grants-2012_09
Patent number
US08263609B2

Linked notes

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