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

HRID 2272577Notes

Reaction equation

HRID 2272577 reaction equation
[CH2:1]([N:5]1[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([N+:18]([O-])=O)[CH:10]=2)[CH:2]([CH3:4])[CH3:3].CO.[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([N:5]1[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([NH2:18])[CH:10]=2)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 867297359-isobutyl-6-nitro-2,3,4,9-tetrahydro-1H-carbazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 867297369-isobutyl-2,3,4,9-tetrahydro-1H-carbazol-6-amineYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound obtained in Step 1 (290 mg, 1.06 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-isobutyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine (237 mg, 0.977 mmol, 92%) 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-a15899acb0424eb680d6828ec05da8bd
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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