Methanol → 9-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine

HRID 2272574Notes

Reaction equation

HRID 2272574 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][CH2:18][CH3:19])[C:12]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]2=1)([O-])=O.CO.[H][H]>[Pd].C(OCC)(=O)C>[CH2:17]([N:13]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]2[C:14]1=[CH:15][CH:16]=[C:4]([NH2:1])[CH:5]=2)[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 887MethanolHCID 867297326-nitro-9-propyl-2,3,4,9-tetrahydro-1H-carbazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 867297339-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-amineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound obtained in Step 1 (270 mg, 1.05 mmol) and 10% palladium on carbon (50% wet, 10 mg, 0.09 mmol) in a mixed solvent of methanol (4 mL) and ethyl acetate (4 mL) was stirred at room temperature for 14 hr under 1 atm of hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to give 9-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine (230 mg, 1.006 mmol, 96%) as a brown oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-848f226c00814d279d054cff3954037d
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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